Ethylmorpholine → N2 [3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1-phenyl-L-prolinamide

HRID 1757719ノート

反応式

HRID 1757719 の反応式
C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=[N:23][NH:22]C=2C=CC=1.C(N1CCOCC1)C.N#N.[NH2:36][C@@H:37]([CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C@H:38]([OH:54])[CH2:39][C@@:40]1([C:51]([NH2:53])=[O:52])[CH2:44][CH2:43][CH2:42][N:41]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[CH2:62]([O:69][C:70]([NH:72][C@H:73]([C:78](O)=[O:79])[CH2:74][C:75](=[O:77])[NH2:76])=[O:71])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>C(OCC)(=O)C.O1CCCC1>[N:22]#[N:23].[CH2:62]([O:69][C:70]([NH:72][C@H:73]([C:78]([NH:36][C@@H:37]([CH2:55][C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)[C@H:38]([OH:54])[CH2:39][C@@:40]1([C:51]([NH2:53])=[O:52])[CH2:44][CH2:43][CH2:42][N:41]1[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:79])[CH2:74][C:75](=[O:77])[NH2:76])=[O:71])[C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1

参加物

8

反応物 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 75314Benzyloxycarbonyl-asparagineHCID 86746222N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1-phenyl-L-prolinamideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 86746220N2 [3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1-phenyl-L-prolinamide収率 42.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

0.208 g of dicyclohexylcarbodiimide, 0.124 g of hydroxybenzotriazole and 0.106 g of N-ethylmorpholine were added to a stirred solution of 0.315 g of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -phenyl-L-prolinamide and 0.244 g of N-(benzyloxycarbonyl)-L-asparagine in10 ml of tetrahydrofuran at 0° C. The mixture was stirred for 16 hours, then diluted with ethyl acetate and filtered. The filtrate was washed with sodium bicarbonate solution and sodium chloride solution and the solvent was then removed by evaporation. The residue was chromatographed on silica gel using dichloromethane/methanol (9:1) for theelution to give 0.22 g of N2 -[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -phenyl-L-prolinamide in the form of a white solid of meltingpoint 169°-171° C. (from methanol).

後処理

  1. filtrationfiltered
  2. washThe filtrate was washed with sodium bicarbonate solution and sodium chloride solution
  3. customthe solvent was then removed by evaporation
  4. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-a78ffc9a30f04a34967718950a487a29
出典データセット
uspto-grants-1995_08
特許番号
US05446161

反応ノート

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