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

HRID 720928

Reaction equation

HRID 720928 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][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][CH:23]([NH:38][C:39](=[O:41])[CH3:40])[C:22]=2[CH:42]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([NH: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][CH:23]([NH:38][C:39](=[O:41])[CH3:40])[C:22]=2[CH:42]=1)=[O:16])[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 736104N-carbobenzyloxyalanineHCID 21893886N-[3-amino-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide

Product 1

HCID 53986515N-[3-((N-benzyloxycarbonylalanyl)amino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamideYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-benzyloxycarbonyl-(L)-alanine (63 mg, 0.28 mmol) in dichloromethane (4 ml) at −20° C. was treated with N-[3-amino-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]acetamide (100 mg, 0.28 mmol), (V. Fernholz Justus Liebigs Ann., 1950, 568, 63–72), and 1,3-dicylcohexylcarbodiimide (134 mg, 0.31 mmol) and the solution stirred for 16 hours at ambient temperature. Solvent was evaporated under reduced pressure and the residue chromatographed on silica gel, eluting with ethyl acetate to give a white solid which was triturated with diethyl ether. The title compound (85 mg) was obtained as a white solid.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customthe residue chromatographed on silica gel
  3. washeluting with ethyl acetate
  4. customto give a white solid which
  5. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-73a4526c274b4d4a8eba921e461652a5
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Linked notes

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