N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → BocGly-DLeu-MetNH2

HRID 2418536Notes

Reaction equation

HRID 2418536 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][C:3]([O:5]N1C(=O)CCC1=O)=O.[NH2:20][C@@H:21]([C:26]([NH:28][C@H:29]([C:34]([NH2:36])=[O:35])[CH2:30][CH2:31][S:32][CH3:33])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24]>>[NH:1]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:2][C:3]([NH:20][C@@H:21]([C:26]([NH:28][C@H:29]([C:34]([NH2:36])=[O:35])[CH2:30][CH2:31][S:32][CH3:33])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:5]

Participants

3

Reactant 2

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 12952804HDLeu-MetNH2

Product 1

HCID 15602548BocGly-DLeu-MetNH2Yield 95%

Procedure

Condensation of BocDLeuOH (2.49 g.) and HMetNH2 (1.85 g.) by the mixed anhydride method using isobutyl chloroformate gave BocDLeu-MetNH2 in 47% yield. De-t-butoxycarbonylation of BocDLeu-MetNH2 (1.70 g.) using hydrogen chloride in acetic acid gave HDLeu-MetNH2 in 78% yield. Condensation of BocGlyOSu (1.8 g.) and HDLeu-MetNH2 (1.0 g.) by the activated ester method gave BocGly-DLeu-MetNH2 in 95% yield. De-t-butoxycarbonylation of BocGly-DLeu-MetNH2 (1.35 g.) using hydrogen chloride in acetic acid gave HGly-DLeu-MetNH2 in 55% yield.

Sources & evidence

ORD record
ord-8a58808645df4ca7a444781a44c66139
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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