Water → HCID 68550932, compound

HRID 1868132Notes

Reaction equation

HRID 1868132 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[S:21][C:20]([N:22]4[CH2:26][CH2:25][CH2:24][CH:23]4[C:27]([O:29]C(C)(C)C)=[O:28])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C@H:10]([CH3:34])[CH2:9]2)=[C:4]([C:35]([F:38])([F:37])[F:36])[CH:3]=1.CC#N.O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[S:21][C:20]([N:22]4[CH2:26][CH2:25][CH2:24][CH:23]4[C:27]([OH:29])=[O:28])=[CH:19][CH:18]=3)(=[O:15])=[O:16])[C@H:10]([CH3:34])[CH2:9]2)=[C:4]([C:35]([F:38])([F:36])[F:37])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6342AcetonitrileHCID 68551930HCID 68551930, compound

Product 1

HCID 68550932HCID 68550932, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 1-(5-((R)-4-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methylpiperazin-1-ylsulfonyl)thiophen-2-yl)pyrrolidine-2-carboxylate (316.0 mg, 0.547 mmol), CeCl3.7H2O (815.0 mg, 2.19 mmol) and KI (363.0 mg, 2.19 mmol) charged to a microwave vial were added with CH3CN (12 mL) and water (0.2 mL). The reaction mixture was subjected to microwave irradiation at 110° C. for 1 hour. This reaction was repeated twice. Both reaction mixtures were then combined and the supernatant clear solution was transferred into a flask, added with CH2Cl2 and stirred at room temperature. Solid was filtered off, filtrate concentrated, dried under high vacuum to yield crude 1-(5-((R)-4-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methylpiperazin-1-ylsulfonyl)thiophen-2-yl)pyrrolidine-2-carboxylic acid which will be used as it is for the next step.

Workup

  1. customirradiation at 110° C. for 1 hour
  2. customBoth reaction mixtures
  3. customthe supernatant clear solution was transferred into a flask
  4. filtrationSolid was filtered off
  5. concentrationfiltrate concentrated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-375d825e0cf9496e8338b9fc959bba71
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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