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

HRID 720929Notes

Reaction equation

HRID 720929 reaction equation
C(OC([NH:11][C@H:12]([C:14]([NH:16][C:17]1[CH:18]=[CH:19][C:20]2[C:26]3[C:27]([O:35][CH3:36])=[C:28]([O:33][CH3:34])[C:29]([O:31][CH3:32])=[CH:30][C:25]=3[CH2:24][CH2:23][CH:22]([NH:37][C:38](=[O:40])[CH3:39])[C:21]=2[CH:41]=1)=[O:15])[CH3:13])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@H:12]([C:14]([NH:16][C:17]1[CH:18]=[CH:19][C:20]2[C:26]3[C:27]([O:35][CH3:36])=[C:28]([O:33][CH3:34])[C:29]([O:31][CH3:32])=[CH:30][C:25]=3[CH2:24][CH2:23][CH:22]([NH:37][C:38](=[O:40])[CH3:39])[C:21]=2[CH:41]=1)=[O:15])[CH3:13]

Participants

4

Reactant 1

HCID 53986515N-[3-((N-benzyloxycarbonylalanyl)amino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide

Product 1

HCID 69586596N-[3-(alanylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamideYield 65.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of N-[3-((N-benzyloxycarbonylalanyl)amino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide (70 mg, 0.125 mmol), (prepared as described in Example 1), in ethanol (2 ml) was hydrogenated at atmospheric pressure over 5% palladium on carbon (10 mg) for 2 hours. Ethanol (3 ml) was added and the solution was filtered through diatomaceous earth and the filtrate concentrated under reduced pressure. Trituration with ethyl acetate/diethyl ether gave the title compound (35 mg) as a white solid.

Workup

  1. filtrationthe solution was filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-18ecf6c6d2cd4e40bc9f4103e3fe8c2d
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

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