Dicyclohexylcarbodiimide → N-[1-oxo-2-[5-[2-(2H-tetrazol-5-yl]phenyl]-1H-benzimidazol-1-yl]octyl]-L-serine

HRID 743903Notes

Reaction equation

HRID 743903 reaction equation
C[O:2][C:3](=[O:8])[C@H:4]([CH2:6][OH:7])[NH2:5].C(N(C(C)C)CC)(C)C.[N:18]1[NH:19][N:20]=[N:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:47]=[CH:46][C:32]2[N:33]([CH:36]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:37](O)=[O:38])[CH:34]=[N:35][C:31]=2[CH:30]=1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>>[O:38]=[C:37]([NH:5][C@H:4]([C:3]([OH:2])=[O:8])[CH2:6][OH:7])[CH:36]([N:33]1[C:32]2[CH:46]=[CH:47][C:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[C:22]3[N:18]=[N:19][NH:20][N:21]=3)=[CH:30][C:31]=2[N:35]=[CH:34]1)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

6

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 2723731(S)-methyl 2-amino-3-hydroxypropanoateHCID 158381802-[5-[2-(2H-tetrazol-5-yl)phenyl]benzimidazol-1-yl]octanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 69962688N-[1-oxo-2-[5-[2-(2H-tetrazol-5-yl]phenyl]-1H-benzimidazol-1-yl]octyl]-L-serineYield 10.6%

Procedure

Serine methyl ester (1.0 mmoles, 0.119 g ), diisopropylethylamine (1.0 mmoles, 0.206 g), 2-[5-[2-(2H-tetrazol-5-yl)phenyl]-1H-benzimidazol-1-yl]octanoic acid (1.0 mmoles, 0.405 g), hydroxybenzotriazole (1.0 mmole, 0.135 g), and dicyclohexylcarbodiimide (1.0 mmoles, 0.206 g) were reacted as in Example 37. The resulting ester 0.19 moles, 0.097 g) was hydrolyzed as in Example 37 to yield 0.052 g of N-[1-oxo-2-[5-[2-(2H-tetrazol-5-yl]phenyl]-1H-benzimidazol-1-yl]octyl]-L-serine (MS).

Sources & evidence

ORD record
ord-441558ce066441f08bc3c51fd5f58d60
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

Loading…