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

HRID 2171926노트

반응식

HRID 2171926 반응식
[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]

참가 물질

5

반응물 2

HCID 23707502Potassium hydroxy sulfiteHCID 86714775(S)-tert-Butyl 2-(2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethyl-butylthio)ethanoate2회

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bc84fd47ee344a6a8e3189c2b0b81161
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051319B2

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