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Benzyl chloroformate → 2-{[(Benzyloxy)carbonyl]amino}adamantane-2-carboxylic acid

HRID 582794
ノート
印刷プレビュー

反応式

HRID 582794 の反応式
[NH2:1][C:2]1([C:12]([OH:14])=[O:13])[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[CH2:27]([O:34][C:35](Cl)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:27]([O:34][C:35]([NH:1][C:2]1([C:12]([OH:14])=[O:13])[CH:9]2[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]1[CH2:11]3)[CH2:10]2)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 643542-Aminoadamantane-2-carboxylic acidHCID 11708267Bistrimethylsilylacetamid

生成物 1

HCID 221118642-{[(Benzyloxy)carbonyl]amino}adamantane-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

1.015 g of 2-amino-2-adamantanecarboxylic acid and 6 ml of bis(trimethylsilyl)acetamide in 10 ml of DCM is heated to reflux for one and a half hours. 0.75 ml of benzyloxycarbonyl chloride is added and the mixture is heated at 50° C. for 15 minutes. The reaction medium is cooled to -70° C., decomposition is then effected by adding ice and the mixture is extracted with AcOEt. The organic phase is washed with water (twice) and with brine, dried over MgSO4 and evaporated under vacuum. The product crystallizes in hexane; 1.164 g are obtained.

後処理

  1. temperatureto reflux for one and a half hours
  2. temperatureThe reaction medium is cooled to -70° C.
  3. additionby adding ice
  4. extractionthe mixture is extracted with AcOEt
  5. washThe organic phase is washed with water (twice) and with brine
  6. dry with materialdried over MgSO4
  7. customevaporated under vacuum
  8. customThe product crystallizes in hexane
  9. custom1.164 g are obtained

出典と根拠

ORDレコード
ord-ab6aa8bba20b4564af53528c2da65ace
出典データセット
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05925661

反応ノート

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