Chloroform → Z-Leu-Phe-CO2Bu

HRID 1757134Notes

Reaction equation

HRID 1757134 reaction equation
[NH:1]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=O)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].N([C:55]([O:57][CH2:58][C:59]1C=CC=[CH:61][CH:60]=1)=[O:56])[C@H](C(N[C@H](C(C(OCC)=O)=O)CC1C=CC=CC=1)=O)CC(C)C.C(OCCCC)CCC.[Na].C(Cl)(Cl)Cl>C(O)CCC.CO>[NH:1]([C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([C:55]([O:57][CH2:58][CH2:59][CH2:60][CH3:61])=[O:56])=[O:20])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 7408339Z-Leu-phe-OHHCID 131719097Z-Leu-Phe-CO2EtHCID 131719098Sodium butyloxide

Product 1

HCID 131719096Z-Leu-Phe-CO2BuYield 43%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 887MethanolSolvent

Procedure

This compound was prepared from Z-Leu-Phe-OH and butyl oxalyl chloride in 43% yield by the procedure described for the synthesis of Z-Leu-Phe-CO2Et, except that butyl oxalyl chloride was used in place of ethyl oxalyl chloride and sodium butyloxide in butanol was used for enol ester hydrolysis. Single spot on TLC, Rf =0.54 (CHCl3 :CH3OH=50:1) MS(FAB) m/e=497 (m+1), 1H NMR (CDCl3) ok.

Sources & evidence

ORD record
ord-801e518cc01e455f9577de8bd85c0d8f
Source dataset
uspto-grants-1995_08
Patent number
US05444042

Reaction notes

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