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

HRID 278038노트

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HRID 278038 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bcd7af2279944b34bd8f897fe6c1606b
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358978B1

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