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

HRID 2040501노트

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HRID 2040501 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

(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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-d7450f449dfd4b95933c3eed2ff72f76
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580859B2

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