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

HRID 1055132ノート

反応式

HRID 1055132 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0c6a8f14740c4a75945241fb19a2455e
出典データセット
uspto-grants-2016_07
特許番号
US09394302B2

反応ノート

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