Dicyclohexylcarbodiimide → BocPro-MePhe-PheOBz

HRID 2418618Notes

Reaction equation

[N:1]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][CH2:18][C@H:2]1[C:3]([N:5]([CH3:17])[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].[NH2:28][C@H:29]([C:38]([O:40][C:41]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:42])=[O:39])[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34]C=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[N:1]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][CH2:18][C@H:2]1[C:3]([N:5]([CH3:17])[C@H:6]([C:14]([NH:28][C@H:29]([C:38]([O:40][C:41]([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:42])=[O:39])[CH2:30][C:31]1[CH:32]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 80170N-Hydroxysuccinimide

HCID 131713807BocPro-MePheOH

HCID 131713809HPheOBz

Product 1

HCID 131713808BocPro-MePhe-PheOBzYield 76%

Procedure

Condensation of BocProOH (4.30 g.) and HMePheOMe (2.74 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocPro-MePheOMe in 77% yield. Demethylation of BocPro-MePheOMe (3.0 g.) using aqueous sodium hydroxide gave BocPro-MePheOH in 83% yield. Condensation of BocPro-MePheOH (1.71 g.) and HPheOBz (2.14 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-MePhe-PheOBz in 76% yield. Debenzylation of BocPro-MePhe-PheOBz (2.0 g.) by hydrogenation with palladium catalyst gave BocPro-MePhe-PheOH in 100% yield.

Sources & evidence

ORD record: ord-12a9fcca10cc478da64f7bdbec1a9772
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

Loading…