Triphenylphosphine → n-[(5s)-3-(2-Morpholinoethoxy)-9,10,11-trimethoxy-6,7-dihydro-5h-dibenzo[a,c]cyclohepten-5-yl]acetamide

HRID 720938

반응식

HRID 720938 반응식
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.[CH3:41][C:42]([NH:44][CH:45]1[C:55]2[CH:56]=[C:57](O)[CH:58]=[CH:59][C:54]=2[C:53]2[C:48](=[CH:49][C:50]([O:65][CH3:66])=[C:51]([O:63][CH3:64])[C:52]=2[O:61][CH3:62])[CH2:47][CH2:46]1)=[O:43]>ClCCl>[O:38]1[CH2:39][CH2:40][N:35]([CH2:34][CH2:33][O:32][C:57]2[CH:58]=[CH:59][C:54]3[C:53]4[C:52]([O:61][CH3:62])=[C:51]([O:63][CH3:64])[C:50]([O:65][CH3:66])=[CH:49][C:48]=4[CH2:47][CH2:46][C@H:45]([NH:44][C:42](=[O:43])[CH3:41])[C:55]=3[CH:56]=2)[CH2:36][CH2:37]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 97865N-AcetylcolchicinolHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 9825978n-[(5s)-3-(2-Morpholinoethoxy)-9,10,11-trimethoxy-6,7-dihydro-5h-dibenzo[a,c]cyclohepten-5-yl]acetamide수율 37%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

DEAD (0.118 g; 0.75 mmol), triphenylphosphine (0.196 g; 0.75 mmol) and 4-(2-hydroxyethyl)morpholine (61 μl; 0.5 mmol) were added to a solution of N-acetyl-colchicinol (0.178 g; 0.5 mmol) in dichloromethane (5 ml) under argon atmosphere. The mixture was stirred at ambient temperature for 6 hours. After evaporation the residue was purified by flash chromatography eluting with a gradient of 2–10% ethanol/dichloromethane to give N-[(5S)-3-(2-morpholinoethoxy)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide.

후처리

  1. customAfter evaporation the residue
  2. customwas purified by flash chromatography
  3. washeluting with a gradient of 2–10% ethanol/dichloromethane

출처 및 근거

ORD 기록
ord-e3310b1a05b744c28a04a24dbd251ad1
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135502B1

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