Water → (S)-tert-Butyl 2-(2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethylbutyl-sulfonyl)ethanoate

HRID 2171924Notes

Reaction equation

HRID 2171924 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.[OH2:31]>CO>[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]([CH3:23])([CH3:24])[CH3:25])=[O:20])(=[O:1])=[O:31])[C:11]([F:30])=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 23707502Potassium hydroxy sulfiteHCID 86714775(S)-tert-Butyl 2-(2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethyl-butylthio)ethanoate2×

Product 1

HCID 86714776(S)-tert-Butyl 2-(2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethylbutyl-sulfonyl)ethanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Oxone (5.37 g, 8.73 mmol) was added to a solution of (S)-tert-Butyl 2-(2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethyl-butylthio)ethanoate, 168a, (1.10 g, 2.91 mmol) in methanol (50 mL) and water (20 mL) and the solution was stirred 3 hours at room temperature. The solution was concentrated in vacuo to give a white residue that was dissolved in water (100 mL). The aqueous layer was extracted with EtOAc (3×50 mL) and the combined organic phases was dried (MgSO4), filtered and concentrated in vacuo to afford 750 mg of the desired product as a white solid: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=1.29 minutes (M+H) 410.19.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto give a white residue that
  3. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
  4. dry with materialthe combined organic phases was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93f00972030848a7877ea45759f17c4f
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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