Preparation of N-unsubstituted β-ketoamides by Rhodococcus rhodochrous-catalysed hydration of β-ketonitriles

Tetrahedron

Volumn 60, Issue 3, 2004, Pages 607-618

  Gotor, Vicente ^a   Liz, Ramón ^a   Testera, Ana Ma ^a,b  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Amido ketones; Enzyme inhibitors; Microbial reactions; Rhodococcus rhodochrous; Tautomerism

Indexed keywords

2 BENZOYLBUTANAMIDE; 3 (1 METHYLINDOL 3 YL) 3 OXOPROPANAMIDE; 3 (2 FURYL) 3 OXOPROPANAMIDE; 3 (3 CHLOROPHENYL) 3 OXOPROPANAMIDE; 3 (3 FURYL) 3 OXOPROPANAMIDE; 3 (3 METHYLPHENYL) 3 OXOPROPANAMIDE; 3 (3,4 DICHLOROPHENYL) 3 OXOPROPANAMIDE; 3 (4 CHLOROPHENYL) 3 OXOPROPANAMIDE; 3 (4 METHOXYPHENYL) 3 OXOPROPANAMIDE; 3 (4 METHYLPHENYL) 3 OXOPROPANAMIDE; 3 OXO 2 PHENYLBUTANAMIDE; 3 OXO 3 (2 THIENYL)PROPANAMIDE; 3 OXO 3 (3 PYRIDYL)PROPANAMIDE; 3 OXO 3 PHENYLPROPANAMIDE; 3 OXO 3 [(3 TRIFLUOROMETHYL)PHENYL]PROPANAMIDE; 3 OXOHEXANAMIDE; 4 (1 METHYLPYRROL 2 YL)METHYL 3 OXOBUTANAMIDE; 4,4 DIMETHYL 3 OXOPENTANAMIDE; AMIDASE; AMIDE; NITRILE; NITRILE HYDRATASE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL STRAIN; BIOTRANSFORMATION; CATALYSIS; GROWTH CURVE; HYDRATION; NONHUMAN; PRIORITY JOURNAL; RHODOCOCCUS;

BACTERIA (MICROORGANISMS); RHODOCOCCUS RHODOCHROUS;

EID: 0347595454     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.096     Document Type: Article

References (87)

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55. 28c.
56. We assume that the remaining 16% includes the formed β-ketoacid 3d and small losses during the work-up.
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58. See for example: (a) Bunting J.W., Kanter J.P. J. Am. Chem. Soc. 115:1993;11705-11715 (b) Yamasaki K., Kajimoto O. Chem. Phys. Lett. 172:1990;271-274 (c) Kallury K.R., Krull U.J., Thompson M. J. Org. Chem. 53:1988;1320-1322 (d) Zheglova D.K., Aleksiev A.A., Kmetska G.G., Petrov G.N., Kol'tsov A.I. J. Org. Chem. USSR. 24:1988;1641-1643 (e) Mills S.G., Beak P. J. Org. Chem. 50:1985;1216-1224 (f) Billman J.H., Sojka S., Taylor P.R. J. Chem. Soc., Perkin Trans. 2. 1972;2034-2035 (g) Allen G., Dwek R.A. J. Chem. Soc. (B). 1966;161-163 (h) Burdett J.L., Rogers M.T. J. Am. Chem. Soc. 86:1964;2105-2109.
59. See for example: (a) Bunting J.W., Kanter J.P. J. Am. Chem. Soc. 115:1993;11705-11715 (b) Yamasaki K., Kajimoto O. Chem. Phys. Lett. 172:1990;271-274 (c) Kallury K.R., Krull U.J., Thompson M. J. Org. Chem. 53:1988;1320-1322 (d) Zheglova D.K., Aleksiev A.A., Kmetska G.G., Petrov G.N., Kol'tsov A.I. J. Org. Chem. USSR. 24:1988;1641-1643 (e) Mills S.G., Beak P. J. Org. Chem. 50:1985;1216-1224 (f) Billman J.H., Sojka S., Taylor P.R. J. Chem. Soc., Perkin Trans. 2. 1972;2034-2035 (g) Allen G., Dwek R.A. J. Chem. Soc. (B). 1966;161-163 (h) Burdett J.L., Rogers M.T. J. Am. Chem. Soc. 86:1964;2105-2109.
60. See for example: (a) Bunting J.W., Kanter J.P. J. Am. Chem. Soc. 115:1993;11705-11715 (b) Yamasaki K., Kajimoto O. Chem. Phys. Lett. 172:1990;271-274 (c) Kallury K.R., Krull U.J., Thompson M. J. Org. Chem. 53:1988;1320-1322 (d) Zheglova D.K., Aleksiev A.A., Kmetska G.G., Petrov G.N., Kol'tsov A.I. J. Org. Chem. USSR. 24:1988;1641-1643 (e) Mills S.G., Beak P. J. Org. Chem. 50:1985;1216-1224 (f) Billman J.H., Sojka S., Taylor P.R. J. Chem. Soc., Perkin Trans. 2. 1972;2034-2035 (g) Allen G., Dwek R.A. J. Chem. Soc. (B). 1966;161-163 (h) Burdett J.L., Rogers M.T. J. Am. Chem. Soc. 86:1964;2105-2109.
61. See for example: (a) Bunting J.W., Kanter J.P. J. Am. Chem. Soc. 115:1993;11705-11715 (b) Yamasaki K., Kajimoto O. Chem. Phys. Lett. 172:1990;271-274 (c) Kallury K.R., Krull U.J., Thompson M. J. Org. Chem. 53:1988;1320-1322 (d) Zheglova D.K., Aleksiev A.A., Kmetska G.G., Petrov G.N., Kol'tsov A.I. J. Org. Chem. USSR. 24:1988;1641-1643 (e) Mills S.G., Beak P. J. Org. Chem. 50:1985;1216-1224 (f) Billman J.H., Sojka S., Taylor P.R. J. Chem. Soc., Perkin Trans. 2. 1972;2034-2035 (g) Allen G., Dwek R.A. J. Chem. Soc. (B). 1966;161-163 (h) Burdett J.L., Rogers M.T. J. Am. Chem. Soc. 86:1964;2105-2109.
62. See for example: (a) Bunting J.W., Kanter J.P. J. Am. Chem. Soc. 115:1993;11705-11715 (b) Yamasaki K., Kajimoto O. Chem. Phys. Lett. 172:1990;271-274 (c) Kallury K.R., Krull U.J., Thompson M. J. Org. Chem. 53:1988;1320-1322 (d) Zheglova D.K., Aleksiev A.A., Kmetska G.G., Petrov G.N., Kol'tsov A.I. J. Org. Chem. USSR. 24:1988;1641-1643 (e) Mills S.G., Beak P. J. Org. Chem. 50:1985;1216-1224 (f) Billman J.H., Sojka S., Taylor P.R. J. Chem. Soc., Perkin Trans. 2. 1972;2034-2035 (g) Allen G., Dwek R.A. J. Chem. Soc. (B). 1966;161-163 (h) Burdett J.L., Rogers M.T. J. Am. Chem. Soc. 86:1964;2105-2109.
63. See for example: (a) Bunting J.W., Kanter J.P. J. Am. Chem. Soc. 115:1993;11705-11715 (b) Yamasaki K., Kajimoto O. Chem. Phys. Lett. 172:1990;271-274 (c) Kallury K.R., Krull U.J., Thompson M. J. Org. Chem. 53:1988;1320-1322 (d) Zheglova D.K., Aleksiev A.A., Kmetska G.G., Petrov G.N., Kol'tsov A.I. J. Org. Chem. USSR. 24:1988;1641-1643 (e) Mills S.G., Beak P. J. Org. Chem. 50:1985;1216-1224 (f) Billman J.H., Sojka S., Taylor P.R. J. Chem. Soc., Perkin Trans. 2. 1972;2034-2035 (g) Allen G., Dwek R.A. J. Chem. Soc. (B). 1966;161-163 (h) Burdett J.L., Rogers M.T. J. Am. Chem. Soc. 86:1964;2105-2109.
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72. 10g.
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75. 36d.
76. 36c.
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79. See Ref. 35, p 113.
80. See Ref. 35, p 402.
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