Lithium tri-s-butylborohydride → 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]amide

HRID 1698190ノート

反応式

HRID 1698190 の反応式
[CH3:1][S:2]([C:5]1[S:6][C:7](/[C:10](=[N:13]\[S:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])/[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:4])=[O:3].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+]>C1COCC1>[CH3:1][S:2]([C:5]1[S:6][C:7]([C@@H:10]([NH:13][S:14]([C:16]([CH3:17])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:3])=[O:4]

参加物

4

反応物 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 87126692(NZ)-2-methyl-N-[1-(2-methylsulfonyl-1,3-thiazol-5-yl)propylidene]propane-2-sulfinamide

生成物 1

HCID 667274522-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]amide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a chilled (−78° C.) solution of 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide (93 mg, 0.29 mmol) in THF (5 mL) was added a 1 M solution of lithium tri-sec-butylborohydride (L-Selectride) (0.58 mL, 0.58 mmol) in THF dropwise. After 2.5 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride solution (100 mL), and the aqueous layer was separated. The aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes to afford 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-thiazol-5-yl)-propyl]-amide.

後処理

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride solution (100 mL)
  2. customthe aqueous layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a gradient of 0-100% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-6f780b8560a04be8a4e2a4ac4818cd55
出典データセット
uspto-grants-2012_04
特許番号
US08163918B2

反応ノート

読み込み中…