Benzyl chloroformate → N-Cbz-d-alanine

HRID 371805

反応式

HRID 371805 の反応式
[NH2:1][C@@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[OH-].[Na+].[CH2:9]([O:16][C:17](Cl)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([O:16][C:17]([NH:1][C@@H:2]([C:4]([OH:6])=[O:5])[CH3:3])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

4

反応物 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2 回HCID 71080D-Alanine

生成物 1

HCID 70832N-Cbz-d-alanine

反応条件

温度
4 °C

実験手順

Nα -Benzyloxycarbonyl-D-alanine is prepared in the following manner. To a solution of 12.5 g. of D-alanine in 70 ml. of 2N sodium hydroxide, with ice cooling and stirring, is added in simultaneous dropwise addition 24 g. of benzyloxycarbonyl chloride and 35 ml. of 4N sodium hydroxide. The pH is maintained at 10 to 12 using a pH electrode in the reaction vessel. The reaction is stirred for one hour further at 4° C. and then extracted with 100 ml. of ethyl ether and acidified to pH 3 with concentrated hydrochloric acid. The product precipitates and is separated by filtration and dried in air; 23.5 g., m.p. 82°-85° C.; [α]D25 + 14.8° (c. 1, 1N acetic acid). A second crop can be obtained from the filtrate by concentration and cooling.

後処理

  1. additionis added in simultaneous dropwise addition 24 g
  2. temperatureThe pH is maintained at 10 to 12 using a pH electrode in the reaction vessel
  3. extractionextracted with 100 ml
  4. customThe product precipitates
  5. customis separated by filtration
  6. customdried in air
  7. custom[α]D25 + 14.8° (c. 1, 1N acetic acid)
  8. customA second crop can be obtained from the filtrate by concentration
  9. temperaturecooling

出典と根拠

ORDレコード
ord-0dc1313d594d45d9929c79609c6ae7a8
出典データセット
uspto-grants-1978_05
特許番号
US04087418

関連ノート

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