Triphenylphosphine → Methyl (2S)-2-benzyloxycarbonylamino-4-cyanobutyrate

HRID 1289244

반응식

HRID 1289244 반응식
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:16][CH2:17][C:18](=O)[NH2:19])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)(Cl)(Cl)Cl>[CH2:9]([O:8][C:6]([NH:5][C@@H:4]([CH2:16][CH2:17][C:18]#[N:19])[C:3]([O:2][CH3:1])=[O:21])=[O:7])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 7020255Z-Gln-ome

생성물 1

HCID 11000307Methyl (2S)-2-benzyloxycarbonylamino-4-cyanobutyrate

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

A solution of N-benzyloxycarbonyl-L-glutamine methyl ester (25 g) in THF (500 ml) was added dropwise to a stirred solution of triphenylphosphine (44.5 g) in carbon tetrachloride (1 L). The mixture was heated to 50° C. for 2 hours. The mixture was evaporated. The resultant oil was triturated in ethyl acetate. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatogaphy using a 1:1 mixture of hexane and ethyl acetate as eluant. There was thus obtained methyl (2S)-2-benzyloxycarbonylarnino-4-cyanobutyrate (19.38 g, 83%).

후처리

  1. customThe mixture was evaporated
  2. customThe resultant oil was triturated in ethyl acetate
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatogaphy
  6. additiona 1:1 mixture of hexane and ethyl acetate as eluant

출처 및 근거

ORD 기록
ord-ebe61e5660a14d72aaeb847aa9d66948
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05747499

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