Acetic Acid → HCID 57440192, 화합물

HRID 708548노트

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HRID 708548 반응식
[Si]([O:18][CH2:19][C@@H:20]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[OH-].[Na+].C(O)(=O)C>CO.O>[OH:18][CH2:19][C@@H:20]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 131733855(S)-di-tert-butyl (4-((tert-butyldiphenylsilyl)oxy)butane-1,3-diyl)dicarbamate

생성물 1

HCID 57440192HCID 57440192, 화합물수율 48%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
70 °C

실험 절차

To a solution of (S)-di-tert-butyl (4-((tert-butyldiphenylsilyl)oxy)butane-1,3-diyl)dicarbamate (6.25 g, 11.51 mmol) in MeOH (100 mL) was added sodium hydroxide (1.38 g, 34.5 mmol) in water (20.0 mL). The mixture was heated to 70° C. for 18 h then cooled to room temperature and partially concentrated in vacuo. DCM was then added and the mixture was cooled to 0° C., whereupon acetic acid (2.31 mL, 40.3 mmol) was added. The organic layer was then separated, washed with saturated NaHCO3 (aq) and brine. The combined aqueous portions were extracted with DCM and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude residue was purified via silica gel chromatography (EtOAc-Heptane) to afford the title compound (1.67 g, 48%). LCMS: Rt=0.67 min, m/z=305.1 (M+1) Method 2m_acidic. 1H NMR (400 MHz, CDCl3) δ ppm 5.06 (br s, 1H) 4.83 (br s, 1H) 3.82-3.64 (m, 2H) 3.61 (dd, J=10.3, 4.9 Hz, 1H) 3.43-3.25 (m, 1H) 3.11-2.93 (m, 1H) 2.18 (br s, 1H) 1.79-1.65 (m, 1H) 1.64-1.58 (m, 1H) 1.51-1.36 (m, 18H).

후처리

  1. temperaturethen cooled to room temperature
  2. concentrationpartially concentrated in vacuo
  3. additionDCM was then added
  4. additionwas added
  5. customThe organic layer was then separated
  6. washwashed with saturated NaHCO3 (aq) and brine
  7. extractionThe combined aqueous portions were extracted with DCM
  8. dry with materialthe combined organic layers were dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified via silica gel chromatography (EtOAc-Heptane)

출처 및 근거

ORD 기록
ord-3f4877c92254416f832c1cc95e6daa39
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174978B2

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