Trifluoroacetic acid → (2S,4S)-4-azido-pyrrolidine-2-carboxylic acid methyl ester trifluoro-acetate salt

HRID 1477515Notes

Reaction equation

HRID 1477515 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([N:10]=[N+:11]=[N-:12])[CH2:7][N:6]1C(OC(C)(C)C)=O)=[O:4].[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23]>C(Cl)Cl>[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23].[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([N:10]=[N+:11]=[N-:12])[CH2:7][NH:6]1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

Product 1

HCID 89768308(2S,4S)-4-azido-pyrrolidine-2-carboxylic acid methyl ester trifluoro-acetate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2S,4S)-4-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (7.8 g, 28.8 mmol) in methylene chloride (30 mL) was added a mixture of trifluoroacetic acid and methylene chloride (1:5, 20 mL) and the reaction mixture was stirred at room temp. for 16 h. The reaction mixture was concentrated under reduced pressure to give (2S,4S)-4-azido-pyrrolidine-2-carboxylic acid methyl ester trifluoroacetate salt (9.6 g, crude) as a light brown oil. The compound was used in the next step without further purification. MS calcd. for C6H11N4O2 [(M+H)+] 171.0, obsd. 171.2.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-745e91d3ad48464bb2f24d97a15f7ef8
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Reaction notes

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