Potassium hydroxy sulfite → tert-butyl((S)-2(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethylbutylsulfinyl)ethanoate

HRID 1055132Notes

Reaction equation

HRID 1055132 reaction equation
[OH:1]OS([O-])=O.[K+].[Cl:7][C:8]1[N:13]=[C:12]([NH:14][C@@H:15]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:16][S:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:11]([F:30])=[CH:10][N:9]=1>CO.O>[C:22]([O:21][C:19](=[O:20])[CH2:18][S@:17]([CH2:16][CH:15]([NH:14][C:12]1[C:11]([F:30])=[CH:10][N:9]=[C:8]([Cl:7])[N:13]=1)[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:1])([CH3:23])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86714775(S)-tert-Butyl 2-(2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethyl-butylthio)ethanoate2×

Product 1

HCID 131732952tert-butyl((S)-2(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethylbutylsulfinyl)ethanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Oxone (1.04 g, 1.69 mmol) was added to a stirring solution of (S)-tert-Butyl 2-(2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethyl-butylthio)ethanoate, 168a, (0.53 g, 1.41 mmol) in methanol (20 mL). The solution was stirred for 15 minutes at room temperature. The solution was concentrated to give white residue which was dissolved in water (50 mL). The aqueous layer was extracted with EtOAc (3×25 mL) and the organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 540 mg of the desired product as a white solid: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=3.05 minutes (M+H) 394.28.

Workup

  1. concentrationThe solution was concentrated
  2. customto give white residue which
  3. extractionThe aqueous layer was extracted with EtOAc (3×25 mL)
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c6a8f14740c4a75945241fb19a2455e
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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