Dicyclohexylcarbodiimide → HCID 131713749, compound

HRID 2418572Notes

Reaction equation

HRID 2418572 reaction equation
[N:1]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14](O)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[NH2:27][C@H:28]([C:37]([NH:39][CH2:40][C:41]([O:43][C:44]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:45])=[O:42])=[O:38])[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33]C=1.C1(N=C=NC2CCCCC2)CCCCC1>>[N:1]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:27][C@H:28]([C:37]([NH:39][CH2:40][C:41]([O:43][C:44]([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)=[O:45])=[O:42])=[O:38])[CH2:29][C:30]1[CH:31]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 7019898HCID 7019898, compoundHCID 131713750HCID 131713750, compound

Product 1

HCID 131713749HCID 131713749, compoundYield 66%

Procedure

Condensation of BocPro-PheOH (3.12 g.) and HPhe-Gly-OBz (3.50 g.) using dicyclohexylcarbodiimide and N-hydroxynorbornenedicarboximide gave BocPro-Phe-Phe-GlyOBz in 66% yield. Debenzylation of BocPro-Phe-Phe-GlyOBz (3.70 g.) by hydrogenation with palladium catalyst gave BocPro-Phe-Phe-GlyOH in 100% yield.

Sources & evidence

ORD record
ord-f9e15952a47548108a42d493deebfadd
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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