Sodium Sulfide → tert-Butyl thietan-3-ylcarbamate

HRID 660128ノート

反応式

HRID 660128 の反応式
S(O[CH2:6][CH:7]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:8]OS(=O)(=O)C)(=O)(=O)C.[S-2:22].[Na+].[Na+]>C(O)C>[C:18]([O:17][C:15]([NH:14][CH:7]1[CH2:8][S:22][CH2:6]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

参加物

4

反応物 2

HCID 14804Sodium SulfideHCID 108933932-[(tert-Butoxycarbonyl)amino]propane-1,3-diyl dimethanesulfonate

生成物 1

HCID 57415771tert-Butyl thietan-3-ylcarbamate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

A solution of N-(tert-butyloxycarbonyl)-2-amino-1,3-propanediol dimesylate [prepared according to E. Benoist et al., Synthesis 1998, (8), 1113-1118] (25 g, 72.0 mmol) in ethanol (375 ml) is treated with sodium sulfide (Na2S.xH2O 32-38%, 16.82 g, ˜75.4 mmol) and the mixture is stirred at a temperature of 50° C. (bath 60° C.) for 45 minutes. The cooled reaction mixture is concentrated under reduced pressure and the solid residue poured into water, extracted with Et2O, the combined organic layers washed with brine, dried (Na2SO4), filtered, and concentrated. The crude solid product (12.6 g, 92%) is used in the next step without further purification.

後処理

  1. customThe cooled reaction mixture
  2. concentrationis concentrated under reduced pressure
  3. additionthe solid residue poured into water
  4. extractionextracted with Et2O
  5. washthe combined organic layers washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude solid product (12.6 g, 92%) is used in the next step without further purification

出典と根拠

ORDレコード
ord-c59cf31467f74cdaa41619d56ca6a805
出典データセット
uspto-grants-2011_12
特許番号
US08084474B2

反応ノート

読み込み中…