Sodium Thiosulfate → HCID 68806270, compound

HRID 2217446Notes

Reaction equation

HRID 2217446 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@@H:9]1[C:21](=[O:38])[NH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2SC)=[CH:25][C:24]=1[F:37])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:40]1C=C(C=CC=1)C(OO)=O.[O-:50][S:51]([O-:54])(=S)=O.[Na+].[Na+]>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@@H:9]1[C:21](=[O:38])[NH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[S:51]([CH3:40])(=[O:54])=[O:50])=[CH:25][C:24]=1[F:37])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 68805882HCID 68805882, compound

Product 1

HCID 68806270HCID 68806270, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(3-fluoro-2′-methylsulfanyl-biphenyl-4-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (4.1 g, 7.3 mmol) was dissolved in 20 mL EtOAc, added m-chloroperoxybenzoic acid (7.2 g, 29 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 20 minutes the solution was diluted with 100 mL EtOAc, separated layers, washed organics with sat. NaHCO3 (3×100 mL), water (2×100 mL), brine, dried with MgSO4, filtered and concentrated to yield title compound. (4.3 g, 99%) APCI (AP−): 591.3 (M−H)−.

Workup

  1. stirringvigorously stirring
  2. customreaction in order
  3. customto quench peroxide
  4. additionAfter 20 minutes the solution was diluted with 100 mL EtOAc
  5. customseparated layers
  6. washwashed organics with sat. NaHCO3 (3×100 mL), water (2×100 mL), brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c8c9d7a395a743e5ba51b7a9da75da8b
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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