Benzyl Alcohol → (S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl ester

HRID 967611노트

반응식

HRID 967611 반응식
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7]C(O)=O)[C:4](=[O:11])[O:3]1.C([N:15]([CH2:18]C)CC)C.C1([O:26]P(N=[N+]=[N-])(=O)OC2C=CC=CC=2)C=CC=CC=1.[CH2:39]([OH:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1(C)C=CC=CC=1>[CH2:39]([O:46][C:18](=[O:26])[NH:15][CH2:7][C@H:5]1[C:4](=[O:11])[O:3][C:2]([CH3:1])([CH3:12])[O:6]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 641720(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

생성물 1

HCID 67483545(S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethyl)carbamic acid benzyl ester수율 69.9%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To (S)-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-yl)acetic acid (1 g, 5.7 mmol) and triethylamine (0.66 g, 6.5 mmol) in toluene (20 mL) was added phosphorazidic acid diphenyl ester (1.7 g, 6.2 mmol). The solution was heated to reflux for 1 hour. Benzyl alcohol (0.54 g, 5 mmol) was added and reflux was maintained for additional 6 hours. After cooling, the solution was partitioned between ethyl acetate (2×50 mL) and aqueous sodium hydrogen carbonate (10%, 2×50 mL). The organic layers were collected, dried (sodium sulphate) and the solvent removed by evaporation in vacuo to afford 976 mg of crude (S)-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylmethyl)carbamic acid benzyl ester as an oil.

후처리

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 hour
  3. temperaturereflux
  4. temperaturewas maintained for additional 6 hours
  5. temperatureAfter cooling
  6. customthe solution was partitioned between ethyl acetate (2×50 mL) and aqueous sodium hydrogen carbonate (10%, 2×50 mL)
  7. customThe organic layers were collected
  8. dry with materialdried (sodium sulphate)
  9. customthe solvent removed by evaporation in vacuo

출처 및 근거

ORD 기록
ord-bf22093eae7a43e397753d72b3e042eb
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953812B2

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