Urea → O-(tert-Butyloxycarbonyl-N,O-dimethyl-L-tyrosyl)-N-benzyloxycarbonyl-L-threonine phenacyl ester

HRID 1720093ノート

反応式

HRID 1720093 の反応式
[CH2:1]([O:10][C:11](=[O:27])[C@H:12]([C@@H:24]([CH3:26])[OH:25])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[C:28]([N:35]([CH3:49])[C@H:36]([C:46](O)=[O:47])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C1CCC(N=C=NC2CCCCC2)CC1.NC(N)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:10][C:11](=[O:27])[C@H:12]([C@@H:24]([CH3:26])[O:25][C:46](=[O:47])[C@H:36]([CH2:37][C:38]1[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=1)[N:35]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH3:49])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

参加物

7

反応物 4

HCID 1176UreaHCID 10868DicyclohexylcarbodiimideHCID 7016369N-Boc-N-methyl-4-methoxy-L-phenylalanineHCID 54036068N-Benzyloxycarbonyl-L-threonine phenacyl ester

生成物 1

HCID 54209715O-(tert-Butyloxycarbonyl-N,O-dimethyl-L-tyrosyl)-N-benzyloxycarbonyl-L-threonine phenacyl ester

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
-30 °C

実験手順

2.00 g (5.38 mmol) of (8), 1.67 g (5.4 mmol) of (9) and 70 mg (0.54 mmol) of DMAP were dissolved in 20 ml of CH2Cl2 and cooled to -30° C., and 1.13 g (5.5 mmol) of DCC were added. The mixture .was allowed to reach RT overnight, the urea was filered off, the filtrate was concentrated, the residue was taken up in ether and left to stand for 1 h, and the urea was again filtered off. Sufficiently pure peptolide (10) was obtained by filtration through silica gel with PE/EA 7/3. Yield: 3.5 g (5.28 mmol, 98%), α!D20 =28.7° (c=0.96, CHCl3)

後処理

  1. concentrationthe filtrate was concentrated
  2. waitleft
  3. waitto stand for 1 h
  4. filtrationthe urea was again filtered off

出典と根拠

ORDレコード
ord-11930512da894a79b50f7e176364c371
出典データセット
uspto-grants-1996_04
特許番号
US05504189

反応ノート

読み込み中…