Triethylamine → (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl N-(4-morpholinobutyl)carbamate

HRID 720942

반응식

HRID 720942 반응식
[CH3:1][C:2]([NH:4][CH:5]1[C:15]2[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]=2[C:13]2[C:8](=[CH:9][C:10]([O:25][CH3:26])=[C:11]([O:23][CH3:24])[C:12]=2[O:21][CH3:22])[CH2:7][CH2:6]1)=[O:3].Cl[C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29].C(N(CC)CC)C.[NH2:47][CH2:48][CH2:49][CH2:50][CH2:51][N:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1>ClCCl>[O:55]1[CH2:54][CH2:53][N:52]([CH2:51][CH2:50][CH2:49][CH2:48][NH:47][C:28](=[O:29])[O:20][C:17]2[CH:18]=[CH:19][C:14]3[C:13]4[C:12]([O:21][CH3:22])=[C:11]([O:23][CH3:24])[C:10]([O:25][CH3:26])=[CH:9][C:8]=4[CH2:7][CH2:6][C@H:5]([NH:4][C:2](=[O:3])[CH3:1])[C:15]=3[CH:16]=2)[CH2:57][CH2:56]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 97865N-AcetylcolchicinolHCID 2336114-(Morpholin-4-yl)butan-1-amine

생성물 1

HCID 58658607(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl N-(4-morpholinobutyl)carbamate수율 24%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of N-acetyl-colchicinol (0.357 g; 1 mmol), 4-nitrophenyl chloroformate (0.262 g; 1.3 mmol) and triethylamine (182 μl; 1.3 mmol) in dichloromethane (10 ml) was stirred, under argon atmosphere, at ambient temperature for 90 minutes. 4-(4-Aminobutyl)morpholine (0.237 g; 1.5 mmol) was then added and the mixture was further stirred for 4 hours. After evaporation to dryness the residue was purified by flash chromatography eluting with a gradient of 0–12% ethanol/dichloromethane to give (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl N-(4-morpholinobutyl)carbamate as a white foam.

후처리

  1. customAfter evaporation to dryness the residue
  2. customwas purified by flash chromatography
  3. washeluting with a gradient of 0–12% ethanol/dichloromethane

출처 및 근거

ORD 기록
ord-7d8312511d164d1abc458bb5163f8fd9
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135502B1

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