(2S,3R)-3-Azido-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide trifluoroacetate → (2S,3S)-3-Azido-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide trifluoroacetate

HRID 1527335Notes

Reaction equation

HRID 1527335 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[C:10]([F:27])=[C:11]([CH:24]=[CH:25][CH:26]=1)[CH2:12][NH:13][C:14]([C@@H:16]1[C@H:20]([N:21]=[N+:22]=[N-:23])[CH2:19][CH2:18][NH:17]1)=[O:15].COC([C@@H]1[C@@H](N=[N+]=[N-])CCN1C(OC(C)(C)C)=O)=O>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[C:10]([F:27])=[C:11]([CH:24]=[CH:25][CH:26]=1)[CH2:12][NH:13][C:14]([C@@H:16]1[C@@H:20]([N:21]=[N+:22]=[N-:23])[CH2:19][CH2:18][NH:17]1)=[O:15]

Participants

3

Reactant 2

HCID 86673822(2S,3R)-3-Azido-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide trifluoroacetateHCID 86673823O1-tert-butyl O2-methyl (2S,3S)-3-azidopyrrolidine-1,2-dicarboxylate

Product 1

HCID 71009502(2S,3S)-3-Azido-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide trifluoroacetate

Procedure

was prepared in a similar manner as described in procedure 1 for (2S,3R)-3-azido-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide trifluoroacetate from (2S,3S)-3-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester [361367-99-9]. MS (LC/MS): 298 [M+H]+; tR (HPLC conditions b): 2.68 min.

Workup

  1. customwas prepared in a similar manner
  2. custom2.68 min.

Sources & evidence

ORD record
ord-723300d93d1a416cba4f0417e1c6cd57
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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