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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
ノート
印刷プレビュー

反応式

HRID 720950 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a73e1e672bc84914bfcaf99d161dd913
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07135502B1

反応ノート

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