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Dimethylformamide → N-[(55)-3-carbamoyl-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5yl]acetamide

HRID 720950
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HRID 720950 반응식
C(Cl)(=O)C(Cl)=O.C[N:8]([CH:10]=[O:11])C.C(OC(N[C@H](CCCCNC(OC(C)(C)C)=O)C(NCCC(O[C:29]1[CH:30]=[CH:31][C:32]2[C:38]3[C:39]([O:47][CH3:48])=[C:40]([O:45][CH3:46])[C:41]([O:43][CH3:44])=[CH:42][C:37]=3[CH2:36][CH2:35][C@H:34]([NH:49][C:50](=[O:52])[CH3:51])[C:33]=2[CH:53]=1)=O)=O)=O)(C)(C)C>ClCCl>[C:10]([C:29]1[CH:30]=[CH:31][C:32]2[C:38]3[C:39]([O:47][CH3:48])=[C:40]([O:45][CH3:46])[C:41]([O:43][CH3:44])=[CH:42][C:37]=3[CH2:36][CH2:35][C@H:34]([NH:49][C:50](=[O:52])[CH3:51])[C:33]=2[CH:53]=1)(=[O:11])[NH2:8]
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참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 69586384(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl 3-{[(2R)-2,6-di(tertbutoxycarbonylamino)hexanoyl]amino}propanoate

생성물 1

HCID 58658608N-[(55)-3-carbamoyl-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5yl]acetamide수율 20%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

Oxalyl chloride (0.44 g; 3.4 mmol) and DMF (50 μl) were added to a suspension of N-[(5S)-3-carboxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide (1) under argon atmosphere (1.15 g; 3 mmol) in dichloromethane (10 ml). The mixture was stirred at ambient temperature for 2 hours, evaporated to dryness and redissolved in dichloromethane (20 ml). The solution was cooled at −78° C. and ammonia gas was allowed to bubble through the solution for 5 minutes. The mixture was allowed to warm up and further stirred at ambient temperature for 15 minutes. After evaporation to dryness, the residue was taken up in aqueous sodium hydrogen carbonate/ethyl acetate. The organic phase was separated, evaporated and purified by flash chromatography eluting with ethyl acetate/methanol (95/5) to give N-[(5S)-3-carbamoyl-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide.

후처리

  1. customevaporated to dryness
  2. dissolutionredissolved in dichloromethane (20 ml)
  3. temperatureThe solution was cooled at −78° C.
  4. customto bubble through the solution for 5 minutes
  5. temperatureto warm up
  6. stirringfurther stirred at ambient temperature for 15 minutes
  7. customAfter evaporation to dryness
  8. customThe organic phase was separated
  9. customevaporated
  10. custompurified by flash chromatography
  11. washeluting with ethyl acetate/methanol (95/5)

출처 및 근거

ORD 기록
ord-a73e1e672bc84914bfcaf99d161dd913
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07135502B1

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