1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo [a,c]cyclohepten-5-yl]-2-[2-(butoxycarbonylamino)acetylamino]acetamide

HRID 1761237Notes

Reaction equation

HRID 1761237 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=3[CH2:10][CH2:9][C@H:8]([NH2:23])[C:7]=2[CH:24]=1.[CH3:25][CH2:26]N=C=NCCCN(C)C.[C:36]([O:40][C:41]([NH:43][CH2:44][C:45]([NH:47][CH2:48][C:49]([OH:51])=O)=[O:46])=[O:42])([CH3:39])(C)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]3[C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=3[CH2:10][CH2:9][C@H:8]([NH:23][C:49](=[O:51])[CH2:48][NH:47][C:45](=[O:46])[CH2:44][NH:43][C:41]([O:40][CH2:36][CH2:39][CH2:25][CH3:26])=[O:42])[C:7]=2[CH:24]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 3334662-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acidHCID 11255953(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-ylamine

Product 1

HCID 69732781N-[(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo [a,c]cyclohepten-5-yl]-2-[2-(butoxycarbonylamino)acetylamino]acetamideYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-ylamine [Collect. Czech. Chem. Commun. 1999, 64(2), 217-228] (0.329 g; 1.36 mmol), EDCI (0.230 g; 1.2 mmol); DMAP (0.025 g, 0.2 mmol) and 2[2-(tert-butoxycarbonylamino)acetylamino]acetic acid (0.189 g; 1.2 mmol) in dichloromethane was stirred under argon atmosphere overnight. The resulting precipitate was filtered and washed with ether to give N-[(5S)-3,9,10,11-tetramethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-5-yl]-2-[2-(butoxycarbonylamino)acetylamino]acetamide as a white solid.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with ether

Sources & evidence

ORD record
ord-2265dc1c2f654c44ac314e6fec22ec08
Source dataset
uspto-grants-2005_01
Patent number
US06846925B2

Reaction notes

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