Acetic Acid → HCID 57440192、化合物

HRID 708548ノート

反応式

HRID 708548 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 57440192HCID 57440192、化合物収率 48%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3f4877c92254416f832c1cc95e6daa39
出典データセット
uspto-grants-2015_11
特許番号
US09174978B2

反応ノート

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