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

HRID 1720093

반응식

HRID 1720093 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
-30 °C

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-11930512da894a79b50f7e176364c371
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05504189

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