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

HRID 1527339Notes

Reaction equation

HRID 1527339 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]=[N+:14]=[N-:15])[C@H:9]1[C:16](=[O:27])[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=1[F:26])=O)(C)(C)C.[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29].CO>C(Cl)Cl>[F:31][C:30]([F:33])([F:32])[C:28]([OH:34])=[O:29].[Cl:25][C:21]1[C:20]([F:26])=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][NH:17][C:16]([C@@H:9]1[C@H:10]([N:13]=[N+:14]=[N-:15])[CH2:11][CH2:12][NH:8]1)=[O:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 86673821(2S,3R)-3-Azido-2-(3-chloro-2-fluoro-benzylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86673822(2S,3R)-3-Azido-pyrrolidine-2-carboxylic acid 3-chloro-2-fluoro-benzylamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,3R)-3-azido-2-(3-chloro-2-fluoro-benzylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (560 mg, 1.41 mmol) in CH2Cl2 (8 mL) was added TFA (4 mL), and the solution was stirred at RT for 2 h. Methanol was added then added, and volatiles were removed under reduced pressure. The residue was taken up in methanol and concentrated in vacuo to afford the crude title compound as a yellow resin. MS (LC/MS): 298.0 [M+H]+; tR (HPLC conditions c): 3.59 min. The product was used directly in the next step without further purification.

Workup

  1. additionthen added
  2. customvolatiles were removed under reduced pressure
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52b99ef1625e4fdf86c3ca7bdedeadf6
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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