Trifluoroacetic acid → HCID 86673877, compound

HRID 1527592Notes

Reaction equation

HRID 1527592 reaction equation
C(OC([N:8]1[C@H:13]([C:14](=[O:26])[NH:15][C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=2[F:25])[CH3:17])[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=O)(C)(C)C.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>C(Cl)Cl>[F:30][C:29]([F:32])([F:31])[C:27]([OH:33])=[O:28].[Cl:24][C:20]1[C:19]([F:25])=[C:18]([C@H:16]([NH:15][C:14]([C@@H:13]2[CH2:12][C@@H:11]3[C@@H:9]([CH2:10]3)[NH:8]2)=[O:26])[CH3:17])[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68283823HCID 68283823, compound

Product 1

HCID 86673877HCID 86673877, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,3S,5R)-3-[(R)-1-(3-chloro-2-fluoro-phenyl)-ethylcarbamoyl]-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (3.2 g, 8.36 mmol) in CH2Cl2 (30 mL) was added TFA (15 mL, 195 mmol) and the solution was stirred at RT for 1 h. The crude reaction mixture was concentrated under vacuum, the residue was suspended in MeOH and concentrated again under vacuum. The crude product was used without further purification in the next step. MS (LC/MS): 283.0 [M+H]+; tR (HPLC conditions c): 3.41 min.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under vacuum
  3. concentrationconcentrated again under vacuum
  4. customThe crude product was used without further purification in the next step
  5. custom3.41 min.

Sources & evidence

ORD record
ord-3bb4013cd06547a8b067d31b9b3dcd6d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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