Dicyclohexylcarbodiimide → BocPro-MeDTrp-PheOBz

HRID 2418627Notes

Reaction equation

[N:1]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22][CH2:21][C@H:2]1[C:3]([N:5]([CH3:20])[C@@H:6]([C:17](O)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].[NH2:31][C@H:32]([C:41]([O:43][C:44]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:45])=[O:42])[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37]C=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>>[N:1]1([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[CH2:23][CH2:22][CH2:21][C@H:2]1[C:3]([N:5]([CH3:20])[C@@H:6]([C:17]([NH:31][C@H:32]([C:41]([O:43][C:44]([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)=[O:45])=[O:42])[CH2:33][C:34]1[CH:35]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4]

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 80170N-Hydroxysuccinimide

HCID 131713809HPheOBz

HCID 131713819BocPro-MeDTrpOH

Product 1

HCID 131713820BocPro-MeDTrp-PheOBzYield 83%

Procedure

Condensation of BocProOH (4.63 g.) and MeDTrpOMe (5.00 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocPro-MeDTrpOMe in 69% yield. Demethylation of BocPro-MeDTrpOMe (6.33 g.) using aqueous sodium hydroxide gave BocPro-MeDTrpOH in 77% yield. Condensation of BocPro-MeDTrpOH (3.60 g.) and HPheOBz (3.70 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-MeDTrp-PheOBz in 83% yield. Debenzylation of BocPro-MeDTrp-PheOBz (4.60 g.) by hydrogenation with palladium catalyst gave BocPro-MeDTrp-PheOH in 100% yield.

Sources & evidence

ORD record: ord-b5864f0bc0b043c5a24a2c85c1005787
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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