Trifluoroacetic acid → HCID 58302986, compound

HRID 587386Notes

Reaction equation

HRID 587386 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([N:15]2[CH2:19][C@@H:18]([N:20]([C:22]([O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[O:23])[CH3:21])[C@H:17]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[CH2:16]2)=[O:14])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][C:22](=[O:23])[N:20]([C@H:18]2[C@H:17]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[CH2:16][N:15]([C:13]([CH:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)=[O:14])[CH2:19]2)[CH3:21])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 58303017HCID 58303017, compound

Product 1

HCID 58302986HCID 58302986, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-{(3R,4S)-3-(4-chloro-phenyl)-4-[(4-fluoro-phenoxycarbonyl)-methyl-amino]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1.17 g, 2.14 mmol) in dichloromethane (20 mL) was added at ambient temperature trifluoroacetic acid (1.64 mL, 21.4 mmol) and the reaction mixture was stirred for 3 h. It was treated with an aqueous solution of sodium carbonate (1M, 50 mL) and the organic layer was separated and washed with brine (40 mL). The aqueous layer was extracted with dichloromethane (40 mL) and the combined organic layers were dried over sodium sulfate. Concentration afforded the title compound (760 mg, 79%) as a white semi-solid. MS m/e: 446.1 [M+H]+.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine (40 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (40 mL)
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-8c8a28c1daee488cbf805290c2734ebc
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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