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

HRID 967611

反応式

HRID 967611 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bf22093eae7a43e397753d72b3e042eb
出典データセット
uspto-grants-2005_10
特許番号
US06953812B2

関連ノート

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