Acetic Anhydride → Benzyl (1-cyano-3-phenylpropyl)carbamate

HRID 278038ノート

反応式

HRID 278038 の反応式
[C:1]([CH:4]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=O)[NH2:2].Cl.N[C@H](C(N)=O)CCC1C=CC=CC=1.C(N1C(=O)CCC1=O)(OCC1C=CC=CC=1)=O.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:1]([CH:4]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2]

参加物

6

反応物 4

HCID 7918Acetic AnhydrideHCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylateHCID 18685852L-homophenylalaninamide hydrochlorideHCID 76533771Benzyl (1-carbamoyl-3-phenylpropyl)carbamate

生成物 1

HCID 15946346Benzyl (1-cyano-3-phenylpropyl)carbamate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
75 °C

実験手順

2.78 g of benzyl (1-carbamoyl-3-phenylpropyl)carbamate, prepared from L-homophenylalanine amide hydrochloride and N-Cbz-succinimide, were dissolved in 30 ml of dry pyridine and treated with 6 ml of acetic anhydride. The reaction mixture was stirred at 75° C. for 24 h. The cooled solution was concentrated in vacuo, treated with 100 ml of ethyl acetate, and then extracted three times by shaking with 50 ml each of 5% strength citric acid solution and saturated sodium chloride solution. The organic extract was dried over magnesium sulfate, filtered, concentrated in vacuo, and chromatographed on silica gel using n-heptane/ethyl acetate (1/1). Benzyl (1-cyano-3-phenylpropyl)carbamate was obtained, which was employed in the next stage without further purification.

後処理

  1. concentrationThe cooled solution was concentrated in vacuo
  2. additiontreated with 100 ml of ethyl acetate
  3. extractionextracted three times
  4. stirringby shaking with 50 ml each of 5% strength citric acid solution and saturated sodium chloride solution
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica gel

出典と根拠

ORDレコード
ord-bcd7af2279944b34bd8f897fe6c1606b
出典データセット
uspto-grants-2002_03
特許番号
US06358978B1

反応ノート

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