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

HRID 720950Notes

Reaction equation

HRID 720950 reaction equation
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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a73e1e672bc84914bfcaf99d161dd913
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

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