Sodium Sulfite → sodium (S)-2-(tert-butoxycarbonylamino)-4-(methylthio)butane-1-sulfonate

HRID 2040501ノート

反応式

HRID 2040501 の反応式
CS(O[CH2:6][C@@H:7]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:9][S:10][CH3:11])(=O)=O.[S:20]([O-:23])([O-:22])=[O:21].[Na+:24].[Na+]>CCO.O>[C:16]([O:15][C:13]([NH:12][C@@H:7]([CH2:8][CH2:9][S:10][CH3:11])[CH2:6][S:20]([O-:23])(=[O:22])=[O:21])=[O:14])([CH3:17])([CH3:18])[CH3:19].[Na+:24]

参加物

5

反応物 2

HCID 24437Sodium SulfiteHCID 10358225(S)-2-(tert-butoxycarbonylamino)-4-(methylthio)butyl methanesulfonate

生成物 1

HCID 86656460sodium (S)-2-(tert-butoxycarbonylamino)-4-(methylthio)butane-1-sulfonate収率 37%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

(S)-2-(tert-butoxycarbonylamino)-4-(methylthio)butyl methanesulfonate (1.1 g, 3.51 mmol, 1.0 eq) was dissolved in EtOH (10 mL) and water (8.0 mL). Sodium sulfite (2.21 g, 5.0 eq) was added. The mixture was heated to reflux for 16 hours, and concentrated. The residue was purified by reversed phase column (Diaion HP-20) using distilled water (200 ml) first, then 10% CH3CN in water and finally 20% CH3CN in water to give sodium (S)-2-(tert-butoxycarbonylamino)-4-(methylthio)butane-1-sulfonate (376 mg, 37%). 1H NMR (DMSO-d6, 300 MHz) d 6.75 (d, 1H, NH), 3.50 (br s, 1H, BocNHCH), 2.3-2.5 (m, 4H, SCH2 and OSCH2, overlapped with DMSO solvent peak), 2.0 (s, 3H, SCH3), 1.8 (m, 1H, NHCHCH2CH2S), 1.6 (m, 1H, NHCHCH2CH2S), 1.35 (s, 9H, OC(CH3)3). LC-MS: 2.03 min; MS (ESI−) m/z 298 (M-Na)+, 198 (M-Na-Boc)+.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. concentrationconcentrated
  4. customThe residue was purified by reversed phase column (Diaion HP-20)
  5. distillationusing distilled water (200 ml) first

出典と根拠

ORDレコード
ord-d7450f449dfd4b95933c3eed2ff72f76
出典データセット
uspto-grants-2013_11
特許番号
US08580859B2

反応ノート

読み込み中…