Methanol → HCID 10335685、化合物

HRID 2371419ノート

反応式

HRID 2371419 の反応式
B.CSC.O=[C:6]1[CH:11]([CH2:12][C:13](O)=[O:14])[S:10](=[O:17])(=[O:16])[C:9]2[S:18][C:19]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:20][C:8]=2[NH:7]1.CO>C(COC)OC>[OH:14][CH2:13][CH2:12][CH:11]1[S:10](=[O:16])(=[O:17])[C:9]2[S:18][C:19]([S:21](=[O:23])(=[O:24])[NH2:22])=[CH:20][C:8]=2[NH:7][CH2:6]1

参加物

5

反応物 3

HCID 887MethanolHCID 10359893HCID 10359893、化合物HCID 12423031(Dimethyl sulfide)trihydroboron

生成物 1

HCID 10335685HCID 10335685、化合物

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

Borane-dimethylsulfide (9.5 ml, 10M, 95 mmol) was added to a solution of (2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno-[2,3-b][1,4]thiazin-3-yl)acetic acid (3.25 g, 9.5 mmol) in dimethoxyethane (325 ml) and the resulting solution was heated under reflux for 24 hours. Methanol (100 ml) was added to the cooled reaction mixture, and after stirring for an additional 24 hours, the mixture was evaporated to a thick oil. The oil was partitioned between water and ethyl acetate and the organic layer was washed with brine and dried over sodium sulfate. Removal of the solvent and recrystallization of the residue from water gave 1.5 g. Chromatographic purification over silica gel eluting with CHCl3 /MeOH/NH4OH (70:30:3) gave 3-(2-hydroxyethyl)-2,3-dihydro-4,4-dioxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazine, mp 158°-160° C.

後処理

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 24 hours
  3. customthe mixture was evaporated to a thick oil
  4. customThe oil was partitioned between water and ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent and recrystallization of the residue from water
  8. customgave 1.5 g
  9. customChromatographic purification over silica gel eluting with CHCl3 /MeOH/NH4OH (70:30:3)

出典と根拠

ORDレコード
ord-db83f93778364710ade2433806e4a6f4
出典データセット
uspto-grants-1992_03
特許番号
US05093332

反応ノート

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