Morpholine → N-[(5S)-3-(2-hydroxy-3-morpholinopropoxy)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide

HRID 720943Notes

Reaction equation

HRID 720943 reaction equation
C(OC(N[C@H](CCCCNC(OC(C)(C)C)=O)C(NCCC([O:17][C:18]1[CH:19]=[CH:20][C:21]2[C:27]3[C:28]([O:36][CH3:37])=[C:29]([O:34][CH3:35])[C:30]([O:32][CH3:33])=[CH:31][C:26]=3[CH2:25][CH2:24][C@H:23]([NH:38][C:39](=[O:41])[CH3:40])[C:22]=2[CH:42]=1)=O)=O)=O)(C)(C)C.[NH:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1>CO>[OH:17][CH:18]([CH2:19][N:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1)[CH2:42][O:17][C:18]1[CH:19]=[CH:20][C:21]2[C:27]3[C:28]([O:36][CH3:37])=[C:29]([O:34][CH3:35])[C:30]([O:32][CH3:33])=[CH:31][C:26]=3[CH2:25][CH2:24][C@H:23]([NH:38][C:39](=[O:41])[CH3:40])[C:22]=2[CH:42]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 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 9913914N-[(5S)-3-(2-hydroxy-3-morpholinopropoxy)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamideYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-[(5S)-3-(2,3-epoxypropoxy)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide (1) (0.092 g; 0.22 mmol) and morpholine (40 μl; 0.44 mmol) in methanol was heated at reflux for 4 hours. After evaporation to dryness the residue was purified by flash chromatography eluting with dichloromethane/ethanol (90/10) to give N-[(5S)-3-(2-hydroxy-3-morpholinopropoxy)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide as a yellow foam.

Workup

  1. temperatureat reflux for 4 hours
  2. customAfter evaporation to dryness the residue
  3. customwas purified by flash chromatography
  4. washeluting with dichloromethane/ethanol (90/10)

Sources & evidence

ORD record
ord-300b985e7e054760b756fa48773b9d92
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

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