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Volumn 2, Issue 5, 2005, Pages 404-406

A facile synthesis of chiral isocyanate-phenol and unsymmetrical urea derived from tyrosines without protecting phenolic hydroxyl groups

Author keywords

Di tert butyltricarbonate; DOPA; Isocyanate; Phenol; Tyrosine; Unsymmetrical; Urea

Indexed keywords


EID: 46149102507     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178054406020     Document Type: Review
Times cited : (3)

References (13)
  • 8
    • 46149109196 scopus 로고    scopus 로고
    • Procedure for synthesis of isocyante phenols: L-Tyrosine methyl ester (0.98 g, 5.5 mmol) was added to a solution of DBTC (1.44 g, 5.5 mmol) in dry CH2Cl2 (10 mL) at room temperature under argon atmosphere. After the mixture was stirred for 60 min, the solution was poured into dry n-hexane (1.0 L) to precipiate the title compound. Recrystallization from dry CH2Cl2/ n-hexane (2/1, v/v) gave I-Tyr-OMe as colorless soild. Yield, 1.08 g (98 , Mp, 57-58 °C, α]D25, 43.0° (c, 0.1 g/dL, in CHCl3, 1H NMR (270 MHz, CDCl3, δ, 2.96 (dd, J, 7.02, 13.91 Hz, 1H, CH2, 3.06 (dd, J, 4.59, 13.77 Hz, 1H, CH2, 3.79 (s, 3H, COOCH3, 4.21 (dd, J, 4.59, 7.29 Hz, 1H, >CH, 5.28-5.47 (br, 1H, OH, 6.76 (d, J, 8.64 Hz, 2H, C6H4, 7.03 d, J, 7.8
    • 4: C, 59.73; H, 5.01; N, 6.33. Found: C, 59.72; H,4.98; N, 6.35.
  • 10
    • 46149124942 scopus 로고    scopus 로고
    • L-DOPA isocyanate: Yield, 1.02 g (86 , Mp, 87-88 °C, α]D25, 78.8 °(c, 0.1 g/dL, in CHCl3, 1H NMR (270 MHz, CDCl3, δ, 3.08 (dd, J, 7.29, 13.91 Hz, 1H, CH2, 3.19 (dd, J, 4.59, 13.64 Hz, 1H, CH2, 3.84 (s, 3H, COOCH3, 4.30 (dd, J, 4.59, 7.56 Hz, 1H, >CH, 7.01-7.36 (m, 3H, C6 H3, ppm. 13C NMR (67.5 MHz, CDCl3, δ, 39.15, CH2, 53.26, COOCH3, 58.19 (>CH, 110.38, 111.25, C6H3, 119.38, N=C=O, 125.89, 133.01, 138.66, 142.53, C6H3, 170:70, COOCH3) ppm. IR KBr, v, 3480, OH, 2252, N-C-O, 1735, COOCH3, 1496, 1442, 1242 cm-1. Anal. calcd for CHH11 NO5: C, 55.70; H, 4.67; N, 5.9
    • 5: C, 55.70; H, 4.67; N, 5.90. Found: C, 55.72; H, 4.66; N, 5.92.
  • 13
    • 46149125856 scopus 로고    scopus 로고
    • Synthesis of asymmetric urea: n-Butylamine (99 uL, 1.0 mmol) was added to a solution of I-Tyr-OMe (0.24 g, 1.0 mmol) in dry CH2Cl2 (1.0 mL) at room temperature under nitrogen atmosphere. After the mixture was stirred for 20 min, the solution was concentrated by a rotary evaporator, After that, the residue was purified by silica gel column chromatography eluted with ethyl acetate/ n-hexane (2/1 =v/v) to obtain colorless oil. Yield, 0.27 g (92 , ∐D25, 178.2 °(c, 0.1 g/dL, in CHCl3, 1H NMR (270 MHz, CDCl3, δ, 0.84 (t, J, 7.29 Hz, 3H, CH2CH2 CH2CH3, 1.19-1.44 (4H, CH2H2]CH2CH3, 2.84-3.09 (4H, CH2- and -CH2 C H2 C H2 C H3, 3.66 (s, 3H, COOCH3, 4.68 dd, J, 5.94, 14.04 Hz, 1H, >C
    • -1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.