Dicyclohexylcarbodiimide → HCID 125473419, compound

HRID 2418606Notes

Reaction equation

[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].[NH:17]([CH3:26])[C@H:18]([C:23]([NH2:25])=[O:24])[CH2:19][CH2:20][S:21][CH3:22].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([N:17]([CH3:26])[C@H:18]([C:23]([NH2:25])=[O:24])[CH2:19][CH2:20][S:21][CH3:22])=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 757711-Hydroxybenzotriazole

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

HCID 53947361HCID 53947361, compound

Product 1

HCID 125473419HCID 125473419, compoundYield 81%

Procedure

Condensation of BocLeuOH (5.00 g.) and HMeMetNH2 (4.00 g.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave BocLeu-MeMetNH2 in 81% yield. De-t-butoxycarbonylation of BocLeu-MeMetNH2 (5.96 g.) using hydrogen chloride in ethyl acetate gave HLeu-MeMetNH2 hydrochloride salt in 98% yield. Condensation of BocDTrpOPFP (7.56 g.) and HLeu-MeMetNH2 hydrochloride salt (5.00 g.) by the activated ester method gave BocDTrp-Leu-MeMetNH2 in 56% yield. De-t-butoxycarbonylation of BocDTrp-Leu-MeMetNH2 (2.0 g.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HDTrp-Leu-MeMetNH2 trifluoroacetate salt in 79% yield.

Sources & evidence

ORD record: ord-02c9631d585f4e13afac21b699c6417e
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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