Isobutyl chloroformate → HCID 131713698, compound

HRID 2418530Notes

Reaction equation

HRID 2418530 reaction equation
[C:1]([N:8]([CH3:20])[C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:21][CH2:22][C:23]([O:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27])=[O:24].ClC(OCC(C)C)=O>>[C:1]([N:8]([CH3:20])[C@H:9]([C:17]([NH:21][CH2:22][C:23]([O:25][C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27])=[O:24])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 3

HCID 62365Isobutyl chloroformateHCID 7010602Boc-N-Me-Phe-OHHCID 19099714HCID 19099714, compound

Product 1

HCID 131713698HCID 131713698, compoundYield 52%

Procedure

Condensation of BocMePheOH (5.0 g.) and HGlyOBz (3.75 g.) by the mixed anhydride method using isobutyl chloroformate gave BocMePhe-GlyOBz in 52% yield. De-t-butoxycarbonylation of BocMePhe-GlyOBz (2.0 g.) using hydrogen chloride in ethyl acetate gave HMePhe-GlyOBz in 95% yield.

Sources & evidence

ORD record
ord-f872fcbcbb8e43d8a36b423fa0494648
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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