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Process for preparing Carbamic acid, N-[(1R,4R)-4-amino-5-phenyl-1-(phenylmethyl) pentyl]-, 5-thiazolylmethyl ester

IP.com Disclosure Number: IPCOM000234142D
Publication Date: 2014-Jan-14
Document File: 2 page(s) / 14K

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Process for preparing Carbamic acid, N-[(1R,4R)-4-amino-5-phenyl-1-(phenylmethyl) pentyl]-, 5-thiazolylmethyl ester

   Provided herein is a process for preparing N-[(1R,4R)-4-amino-5-phenyl-1-(phenylmethyl) pentyl]-, 5-thiazolylmethyl ester. The process is described in the following Example.

Example: Preparation of N-[(1R,4R)-4-amino-5-phenyl-1-(phenylmethyl)pentyl]-, 5- thiazolylmethyl ester

Step 1: Preparation of tert-Butyl N-[(1S,3S,4S)-1-benzyl-3-hydroxy-5-phenyl-4- [[(thiazol-5-ylmethoxy)carbonyl]amino]pentyl]carbamate

To a stirred suspension of (thiazol-5-yl) methanol (5.0 g, 0.0434 mol) in DCM (50 mL) at 0°C a solution of carbonyldiimidazole (8.0 g, 0.0493 mol) in DCM (20 mL) is added, followed by triethylamine (7.5 g, 0.0741 mol) addition. The reaction is stirred for 1-2 h, at RT and a solution of tert-butyl (2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2- ylcarbamate (10.95 g, 0.0391 mol) in DCM (20 mL) is added. The reaction mixture is stirred for 2-3 h, at RT and then quenched by addition of water (100 mL), extracted with DCM (2x50 mL) and then washed with 0.5 N aq. HCl (2x75 mL). The DCM layer is dried (Na2SO4), and concentrated under vacuum to give the titled compound. Tert-butyl (2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-ylcarbamate may be prepared for example according to Example 8a of US5654466.

Step 2: Preparation of tert-Butyl N-[(1S,3S,4S)-1-benzyl-3-Mesyloxy-5-phenyl-4- [[(thiazol-5-ylmethoxy)carbonyl]amino]pentyl]carbamate

To a stirred suspension of tert-Butyl N-[(1S,3S,4S)-1-benzyl-3-hydroxy-5-phenyl-4- [[(thiazol-5-ylmethoxy)carbon...