Dicyclohexylcarbodiimide → BocDTrp-Leu-MeNleNH2

HRID 2418621Notes

Reaction equation

[NH:1]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:2]([C:13]([NH:15][C@H:16]([C:21]([OH:23])=O)[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH:31]([CH3:40])[C@H:32]([C:37]([NH2:39])=[O:38])[CH2:33][CH2:34][CH2:35][CH3:36].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>>[NH:1]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:2]([C:13]([NH:15][C@H:16]([C:21]([N:31]([CH3:40])[C@H:32]([C:37]([NH2:39])=[O:38])[CH2:33][CH2:34][CH2:35][CH3:36])=[O:23])[CH2:17][CH:18]([CH3:19])[CH3:20])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

Reactant 4

HCID 10868Dicyclohexylcarbodiimide

HCID 757711-Hydroxybenzotriazole

HCID 55285567MeNleNH2

HCID 131713760BocDTrp-LeuOH

Product 1

HCID 131713814BocDTrp-Leu-MeNleNH2Yield 99%

Procedure

Condensation of BocDTrp-LeuOH (Example 38, 2.09 g.) and MeNleNH2 (1.00 g.) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole gave BocDTrp-Leu-MeNleNH2 in 99% yield. De-t-butoxycarbonylation of BocDTrp-Leu-MeNleNH2 (2.50 g.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HDTrp-Leu-MeNleNH2 in 37% yield.

Sources & evidence

ORD record: ord-f09e40508bcb4b799d77344dda3d8a9c
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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