Benzyl chloroformate → 1-[(Benzyloxy)carbonyl]-3-hydroxyazetidine-3-carboxylic acid

HRID 2049996ノート

反応式

HRID 2049996 の反応式
Cl.[OH:2][C:3]1([C:7]([OH:9])=[O:8])[CH2:6][NH:5][CH2:4]1.[CH2:10]([O:17][C:18](Cl)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[OH-].[Na+].O>[CH2:10]([O:17][C:18]([N:5]1[CH2:6][C:3]([OH:2])([C:7]([OH:9])=[O:8])[CH2:4]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 2

HCID 10387Benzyl chloroformateHCID 670516543-Hydroxyazetidine-3-carboxylic acid hydrochloride

生成物 1

HCID 203431231-[(Benzyloxy)carbonyl]-3-hydroxyazetidine-3-carboxylic acid収率 76.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 14798Sodium Hydroxide溶媒2 回

実験手順

To a solution of 2.5 g (16.3 mmoles) of 3-hydroxyazetidine-3-carboxylic acid (prepared in Example 6) dissolved in a solution of 2.04 g of sodium hydroxide in 54 ml of water is added 3.34 g (1.2 equivalents) of benzyloxycarbonyl chloride under stirring at room temperature, and the mixture is stirred overnight and then mixed with 10% aqueous sodium hydroxide solution. The resulting alkali solution is washed with ether, adjusted to pH 1 with 10% hydrochloric acid and extracted with ether. The extract is washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue is crystallized from n-pentane and then recrystallized from ether-n-pentane to yield 3.137 g of 1-benzyloxycarbonyl-3-hydroxyazetidine-3-carboxylic acid as needles, mp. 134°-136° C., in 76% yield.

後処理

  1. stirringthe mixture is stirred overnight
  2. washThe resulting alkali solution is washed with ether
  3. extractionextracted with ether
  4. washThe extract is washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue is crystallized from n-pentane
  8. customrecrystallized from ether-n-pentane

出典と根拠

ORDレコード
ord-c4912b2aa0bc42f8a4e30a07d463baf4
出典データセット
uspto-grants-1980_04
特許番号
US04199570

反応ノート

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