Trifluoroacetic acid → (2S,4R)-4-Cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic Acid Methyl Ester Trifluoroacetate

HRID 1697713Notes

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1C(OC(C)(C)C)=O)=[O:4].[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>>[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:11])=[O:12])[CH2:7][NH:6]1)=[O:4]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 66771843(2S,4R)-4-cyclopropylmethanesulfonyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 66770846(2S,4R)-4-Cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic Acid Methyl Ester Trifluoroacetate

Procedure

In analogy to the procedure described in example 409f, (2S,4R)-4-cyclopropylmethanesulfonyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (example 423c) was reacted with trifluoroacetic acid to give the title compound as yellow liquid.

Sources & evidence

ORD record: ord-c9bb8d285dad4af9b52adf5f4c5841a1
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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