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

HRID 1289244

反応式

HRID 1289244 の反応式
[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

参加物

5

反応物 2

HCID 11776TriphenylphosphineHCID 7020255Z-Gln-ome

生成物 1

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

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ebe61e5660a14d72aaeb847aa9d66948
出典データセット
uspto-grants-1998_05
特許番号
US05747499

関連ノート

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