4-Methylmorpholine → 2-(N-benzyloxycarbonyl-L-phenylalanyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid

HRID 1590812ノート

反応式

HRID 1590812 の反応式
ClC(OCC(C)C)=O.[CH2:9]([O:16][C:17]([NH:19][C@H:20]([C:28]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([OH:34])=O)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN1CCOCC1.[CH3:45][C:46]1[C:51]([C:52]([OH:54])=[O:53])=[C:50]([NH:55][C:56](=[O:62])[C@H:57]([CH:59]([CH3:61])[CH3:60])[NH2:58])[CH:49]=[CH:48][CH:47]=1>CN(C)C=O.O1CCCC1>[CH2:9]([O:16][C:17]([NH:19][C@H:20]([C:28]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([NH:58][C@H:57]([C:56]([NH:55][C:50]1[CH:49]=[CH:48][CH:47]=[C:46]([CH3:45])[C:51]=1[C:52]([OH:54])=[O:53])=[O:62])[CH:59]([CH3:61])[CH3:60])=[O:34])=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

参加物

7

反応物 4

HCID 79724-Methylmorpholine2 回HCID 62365Isobutyl chloroformateHCID 11899094Z-Phe-pro-OHHCID 541805686-methyl-2-(L-valylamino)benzoic acid

生成物 1

HCID 543276212-(N-benzyloxycarbonyl-L-phenylalanyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid収率 57.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Isobutyl chloroformate (0.17 ml) was added to a tetrahydrofuran solution (3.5 ml) containing N-benzyloxycarbonyl-L-phenylalanyl-L-proline (523 mg) and N-methylmorpholine (0.15 ml) at -15° C., and the mixture was stirred for 0.5 hour. An N,N-dimethylformamide solution (5.5 ml) containing 6-methyl-2-(L-valylamino)benzoic acid (220 mg) and N-methylmorpholine (0.12 ml) was added dropwise to the obtained reaction mixture at -15° C., and the mixture was stirred at this temperature for 0.5 hour and then at room temperature for two hours. The reaction mixture was treated by the same procedures as in item (c) of Example 1 to obtain 2-(N-benzyloxycarbonyl-L-phenylalanyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid (317 mg).

後処理

  1. additionwas added dropwise to the obtained reaction mixture at -15° C.
  2. stirringthe mixture was stirred at this temperature for 0.5 hour
  3. waitat room temperature for two hours

出典と根拠

ORDレコード
ord-8a80297e57d64c4a89ee6570486caeb2
出典データセット
uspto-grants-1993_04
特許番号
US05204462

反応ノート

読み込み中…