Dicyclohexylcarbodiimide → HCID 69960398, compound

HRID 976606Notes

Reaction equation

HRID 976606 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 184 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-benz imidazol-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-8a47be46fb644674a089dae2af7cf430
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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