methyl L-prolinate hydrochloride → 1-[2-(Tert-butoxycarbonyl-methyl-amino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid methyl ester

HRID 1865710Notes

Reaction equation

HRID 1865710 reaction equation
[C:1]([O:5][C:6]([N:8]([C@@H:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=O)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][O:19][C:20](=[O:26])[C@@H:21]1[CH2:25][CH2:24][CH2:23][NH:22]1>>[CH3:18][O:19][C:20]([CH:21]1[CH2:25][CH2:24][CH2:23][N:22]1[C:11](=[O:13])[CH:10]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:9])[CH:14]([CH3:16])[CH3:15])=[O:26]

Participants

3

Reactant 2

HCID 2733200methyl L-prolinate hydrochlorideHCID 7010608Boc-N-methyl-L-valine

Product 1

HCID 690189891-[2-(Tert-butoxycarbonyl-methyl-amino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid methyl esterYield 93.1%

Procedure

Using General Procedure I Method A, (2S)-(tert-Butoxycarbonyl-methyl-amino)-3-methyl-butyric acid (0.37 g, 1.6 mmol) is coupled to L-proline methyl ester hydrochloride (0.26 g, 1.6 mmol) to give 1-[2-(tert-butoxycarbonyl-methyl-amino)-3-methyl-butyryl]-pyrrolidine-2-carboxylic acid methyl ester (0.51 g, 93%) as a white solid.

Sources & evidence

ORD record
ord-86d1825385964ec2814594859dc97a6b
Source dataset
uspto-grants-2009_12
Patent number
US07626023B2

Reaction notes

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