Lipase Catalyzed Regioselective Lactamization as a Key Step in the Synthesis of N-Boc (2R)-1,4-Oxazepane-2-Carboxylic Acid

Organic Process Research and Development

Volumn 18, Issue 9, 2014, Pages 1116-1119

  Aurell, Carl Johan ^a   Karlsson, Staffan ^a   Pontén, Fritiof ^a   Andersen, Søren M ^a  

^a ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS;

BOC PROTECTION; BORANE REDUCTION; CHEMOSELECTIVE; GLYCIDATE; LIPASE-CATALYZED; REGIO-SELECTIVE; ROTATING FLOW; TITLE COMPOUNDS;

REGIOSELECTIVITY;

EID: 84927557475     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op5001644     Document Type: Article

References (11)

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5. At two occations we encountered problems using Pd(OH)2. This could be due to batch variations from different suppliers. Dry palladium(0) on charcoal also works well with methanol in this reduction.
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8. The following enzymes were screened: (a) Candida Antarctica Lipase B (Novozym 435); (b) Porcine Pancreas type II, crude Lipase; (c) Candida Antarctica Lipase A CLEA; (d) Aspergillus spp (protease), Acylase I; (e) Rhizomucor oryzae (Lipozyme RM IM); (f) Candida Cylindracea type VII, Lipase; (g) Pseudomonas fluorescens (Lipase AK Amano); (h) Rhizopus oryzae (Lipase F-AP15); (i) Peniciium camemberti (Lipase G Amano 50); (j) Candida rugosa (Lipase AYS Amano); (k) Aspergillus niger (Lipase AS Amano); (l) Mucor javanicus (Lipase M Amano 10).
9. SpinChem is supplied by Nordic Chem Quest AB, Tvistevägen 48, SE-90736 UmeaÌŠ, Sweden. http://www.spinchem.com.
10. Early introduction of the Boc group was done to avoid the strongly coordinated boron species complexation with the amine moiety which made the work up difficult.
11. Mattsson, S.; Dahlström, M.; Karlsson, S. Tetrahedron Lett. 2007, 48, 2497 - 2499