Sodium Thiosulfate → HCID 68806008, compound

HRID 1796228Notes

Reaction equation

HRID 1796228 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:30])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2SC)=[CH:17][C:16]=1[F:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:32]1C=C(C=CC=1)C(OO)=O.[O-:42][S:43]([O-:46])(=S)=O.[Na+].[Na+]>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:30])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=2[S:43]([CH3:32])(=[O:46])=[O:42])=[CH:17][C:16]=1[F:29])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 68807404HCID 68807404, compound

Product 1

HCID 68806008HCID 68806008, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Fluoro-2′-methylsulfanyl-biphenyl-4-ylcarbamoyl)-pyrrolidine 1-carboxylic acid tert-butyl ester (1.2 g, 2.8 mmol) was dissolved in 30 mL EtOAc, added m-chloroperoxybenzoic acid (3.2 g, 11 mmol) in one portion and stirred at ambient temperature for 3 hours. A 10% aqueous solution (50 mL) of Na2S2O3 was added to the vigorously stirring reaction in order to quench peroxide. After 30 minutes the solution was diluted with 100 mL EtOAc, separated layers, washed organics with sat. NaHCO3 (3×100 mL), brine, dried with MgSO4, filtered and concentrated. Purified on a silica gel column eluted with 50% EtOAc in hexanes. Combined and concentrated pure fractions to yield title compound as a yellow foam. (1.01 g, 78%) APCI (AP−): 461.1 (M−H)−.

Workup

  1. stirringvigorously stirring
  2. customreaction in order
  3. customto quench peroxide
  4. additionAfter 30 minutes the solution was diluted with 100 mL EtOAc
  5. customseparated layers
  6. washwashed organics with sat. NaHCO3 (3×100 mL), brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurified on a silica gel column
  11. washeluted with 50% EtOAc in hexanes
  12. concentrationconcentrated pure fractions

Sources & evidence

ORD record
ord-7334c8ddd6c24350a0fd96a7105907c6
Source dataset
uspto-grants-2006_04
Patent number
US07030141B2

Reaction notes

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