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

HRID 866275Notes

Reaction equation

HRID 866275 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 mole, 0.135 g), and dicyclohexylcarbodiimide (1.0 moles, 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-e004ef0aac4a4aefbda5d1af3fa48890
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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