1-Hydroxybenzotriazole → {[(6-Benzenesulfonyl-naphthalen-1-ylmethyl)-carbamoyl]-methyl}-methyl-carbamic acid benzyl ester

HRID 1715064Notes

Reaction equation

HRID 1715064 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16]([CH2:20][NH2:21])=[CH:15][CH:14]=[CH:13]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:22]([O:29][C:30]([N:32]([CH2:34][C:35](O)=[O:36])[CH3:33])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.ON1C2C=CC=CC=2N=N1.CC[N+](CCCN(C)C)=C=N>C(Cl)Cl.C(N(CC)CC)C>[CH2:22]([O:29][C:30](=[O:31])[N:32]([CH2:34][C:35](=[O:36])[NH:21][CH2:20][C:16]1[C:17]2[C:12](=[CH:11][C:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])=[CH:19][CH:18]=2)[CH:13]=[CH:14][CH:15]=1)[CH3:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 97053N-CarbobenzoxysarcosineHCID 218833923-(Dimethylamino)propyl-ethyl-(iminomethylidene)azaniumHCID 59028770C-(6-Benzenesulfonyl-naphthalen-1-yl)-methylamine

Product 1

HCID 59028785{[(6-Benzenesulfonyl-naphthalen-1-ylmethyl)-carbamoyl]-methyl}-methyl-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of C-(6-benzenesulfonyl-naphthalen-1-yl)-methylamine, (Benzyloxycarbonyl-methyl-amino)-acetic acid, 1-hydroxybenzotriazole, N-(3-dimethylaminopropyl)-N-ethylcarbodiimide and triethylamine in methylene chloride is stirred at room temperature. The reaction is quenched by addition of water, and the mixture is eluted through silica gel to give {[(6-Benzenesulfonyl-naphthalen-1-ylmethyl)-carbamoyl]-methyl}-methyl-carbamic acid benzyl ester.

Workup

  1. customThe reaction is quenched by addition of water
  2. washthe mixture is eluted through silica gel

Sources & evidence

ORD record
ord-cc15183b75a5437b983dc5b53a7b1879
Source dataset
uspto-grants-2010_09
Patent number
US07799797B2

Reaction notes

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