Trifluoroacetic acid → HCID 53312156, compound

HRID 588294Notes

Reaction equation

HRID 588294 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:11][C:10](=[CH2:26])[C:9]1=[O:27])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:17]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:16]=[CH:15][C:14]([CH2:13][C@H:12]2[NH:8][C:9](=[O:27])[C:10](=[CH2:26])[CH2:11]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46193438(R)-5-Biphenyl-4-ylmethyl-3-methylene-2-oxo-pyrrolidine-1-carboxylic acid tert-butylester

Product 1

HCID 53312156HCID 53312156, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(R)-5-Biphenyl-4-ylmethyl-3-methylene-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (4-a, R1=Boc) (509 mg) is dissolved in dichloromethane (10 ml). Mixture is cooled to 0° C. and trifluoroacetic acid (0.5 ml) is added. The mixture is then stirred for 2 h then extracted with saturated sodium carbonate solution (20 ml). Phases are separated. The organic phase is dried (MgSO4) and concentrated to give (R)-5-biphenyl-4-ylmethyl-3-methylenepyrrolidin-2-one (4-a, R1=H). δH (400 MHz, DMSO) 2.47 (1H), 2.68 (1H), 2.74 (1H), 2.87 (1H), 3.87 (1H), 5.22 (1H), 5.64 (1H), 7.33 (3H), 7.45 (2H), 7.60 (2H), 7.65 (2H), 8.32 (1H); m/z (+) 264 ([MH]+, 100%); m/z (+ESI) 264 ([MH]+, 100%).

Workup

  1. extractionthen extracted with saturated sodium carbonate solution (20 ml)
  2. customPhases are separated
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-006e583189724b90a0459dc3e3896276
Source dataset
uspto-grants-2016_01
Patent number
US09227934B2

Reaction notes

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