1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → Boc-prolylproline methyl ester

HRID 346463Notes

Reaction equation

HRID 346463 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:17][O:18][C:19](=[O:25])[C@@H:20]1[CH2:24][CH2:23][CH2:22][NH:21]1>>[CH3:17][O:18][C:19](=[O:25])[C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:10](=[O:12])[C@@H:9]1[CH2:13][CH2:14][CH2:15][N:8]1[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

3

Reactant 2

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 14236281Boc-prolylproline methyl ester

Procedure

2.15 g (10 mmol) BOC-L-proline and 1.66 g (10 mmol) proline methyl ester HCl salt were coupled according to procedure A. Yield of crude product 2.83 g. The product was purified with a silica column using 5% methanol in ethyl acetate as eluent. Yield 2.40 g (7.4 mmol, 74%)

Workup

  1. customThe product was purified with a silica column

Sources & evidence

ORD record
ord-740925e200fc41dd9d586eafdd6a0ca9
Source dataset
uspto-grants-2007_02
Patent number
US07173024B2

Reaction notes

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