Methanol → Methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfonyl}propanoate

HRID 1040081ノート

反応式

HRID 1040081 の反応式
[Br:1][C:2]1[S:6][C:5]([C:7]([S:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])([CH3:9])[CH3:8])=[N:4][CH:3]=1.CO.[OH2:19].[OH2:20].O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[Mg+2]>ClCCl.[O-]S([O-])(=S)=O.[Na+].[Na+].O>[Br:1][C:2]1[S:6][C:5]([C:7]([S:10]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=[O:20])=[O:19])([CH3:9])[CH3:8])=[N:4][CH:3]=1

参加物

7

反応物 3

HCID 887MethanolHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)HCID 58456087Methyl 3-(2-(5-bromothiazol-2-yl)propan-2-ylthio)propanoate

生成物 1

HCID 67258095Methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfonyl}propanoate収率 96%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 24477Sodium Thiosulfate溶媒

実験手順

The product of Step 3 (12.50 g, 38.5 mmol) was taken up in dichloromethane (250 mL)/methanol (125 mL), and magnesium monoperoxyphthalate hexahydrate (35.8 g, 57.8 mmol) was added. The reaction was stirred at room temperature for 2 h. The white slurry was diluted with 10% Na2S2O3 and water and extracted with CH2Cl2 (2×). The combined organic layers were washed with saturated NaHCO3, dried (MgSO4), filtered and evaporated. Flash chromatography (0-40% ethyl acetate in hexanes) afforded 13.12 g (96%) of methyl 3-{[2-(5-bromo-1,3-thiazol-2-yl)propan-2-yl]sulfonyl}propanoate as a white solid. ESI: [M+H]+ m/z 355.9/357.9.

後処理

  1. additionwas added
  2. extractionextracted with CH2Cl2 (2×)
  3. washThe combined organic layers were washed with saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-e6b73bc341a44872ab22c18db3cad024
出典データセット
uspto-grants-2013_10
特許番号
US08551984B2

反応ノート

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