Dicyclohexylcarbodiimide → HCID 69960398, compound

HRID 866280Notes

Reaction equation

HRID 866280 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(C(C)C)CC)(C)C.[N:23]1[NH:24][N:25]=[N:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:52]=[CH:51][C:37]2[N:38]([CH:41]([CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C:42](O)=[O:43])[CH:39]=[N:40][C:36]=2[CH:35]=1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>>[O:43]=[C:42]([NH:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:41]([N:38]1[C:37]2[CH:51]=[CH:52][C:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[C:27]3[N:23]=[N:24][NH:25][N:26]=3)=[CH:35][C:36]=2[N:40]=[CH:39]1)[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

Participants

6

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 12000150L-Phenylalanine, hydrochloride (1:1)HCID 158381802-[5-[2-(2H-tetrazol-5-yl)phenyl]benzimidazol-1-yl]octanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 69960398HCID 69960398, compound

Procedure

L-Phenylalanine hydrochloride (1.75 mmoles, 380 mg), diisopropylethylamine (1.93 mmoles, 0.34 ml), 2-[5-[2-(2H-tetrazol-5-yl)phenyl]-1H-benzimidazol-1-yl]octanoic acid (1.24 mmoles, 0.50 g), hydroxybenzotriazole (1.36 mmoles 187 mg) and dicyclohexylcarbodiimide (1.36 mmoles, 280 mg) were reacted as in Example 37. The stereoisomers were separated by chromatography over silica gel eluted with 2% methanol in chloroform. The isomers were hydrolyzed as in Example 37 to yield N-[1-oxo-2-[5-[2-(2H-tetrazole-5-yl]phenyl]-1H-benzimidazol-1-yl]octyl]-L-phenylalanine.

Workup

  1. customThe stereoisomers were separated by chromatography over silica gel
  2. washeluted with 2% methanol in chloroform

Sources & evidence

ORD record
ord-38513df0ded24b3b8b5084bc542316f9
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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