Diisopropylethylamine → HCID 54404418, compound

Participants

Reaction Steps

(1S-trans)-N-[(3-Carboxy-1,2,2-trimethylcyclopentyl)carbonyl]-4-[(2,6-dichlorobenzoyl)amino]-D-phenylalanine (C26H28Cl2N2O6), 37-C-10 was prepared as follows: To a solution of (1S-trans)-[3-(Phenylmethoxy)carbonyl]-1,2,2-trimethylcyclopentane-1-carboxylic acid, 36-F-1, (503.7 mg) in DMF(5 mL) and DIEA(3 mL) was added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate(731.7 mg) and the reaction stirred at ambient temperature for 1 hour. To the reaction was added 4-[(2,6-dichlorobenzoyl)amino]-D-phenylalanine methyl ester, hydrochloride salt(698.6 mg), 37-B-2, and the reaction stirred for 5 days. The reaction was then diluted with water and extracted with AcOEt. The concentrated extract was purified by flash chromatography on silica gel eluting with methanol in methylene chloride to obtain (1S-trans)-N-[(3-(Phenylmethoxy)carbonyl)-1,2,2-trimethylcyclopentyl)carbonyl]-4-[(2,6-dichlorobenzoyl)amino]-D-phenylalanine methyl ester(1.1024 g). Physical properties as follows: 1H NMR (CDCl3) δ7.82 (1H), 7.58 (2H), 7.28 (8H), 7.05 (2H), 6.07 (1H), 5.06 (2H), 4.74 (1H), 3.66 (3H), 3.07 (3H), 2.05 (3H), 1.53 (1H), 1.21 (3H), 0.90 (3H), 0.75 (3H); MS-ESI (m/z): 637 ([M−H−]); MS-ESI (m/z): 661([M+Na]+).

Provenance & Evidence