1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-hydroxy-2,2-dimethyl-N-(2-{[(2-nitrophenyl)sulfonyl]amino}ethyl)propanamide

HRID 550796Notes

Reaction equation

HRID 550796 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][NH2:16])(=[O:12])=[O:11])([O-:3])=[O:2].[OH:17][CH2:18][C:19]([CH3:24])([CH3:23])[C:20](O)=[O:21].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(Cl)Cl>[OH:21][CH2:20][C:19]([CH3:24])([CH3:23])[C:18]([NH:16][CH2:15][CH2:14][NH:13][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])=[O:17]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 11471557N-(2-Aminoethyl)-2-nitrobenzenesulfonamide

Product 1

HCID 671974123-hydroxy-2,2-dimethyl-N-(2-{[(2-nitrophenyl)sulfonyl]amino}ethyl)propanamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(2-nitrobenzenesulfonyl)ethylenediamine, 3-hydroxy-2,2-dimethylpropionic acid, EDCI, HOBt, methylene chloride, and DMF was stirred at ambient temperature for 4 hours to yield 3-hydroxy-2,2-dimethyl-N-(2-{[(2-nitrophenyl)sulfonyl]amino}ethyl)propanamide. A mixture of this compound, triphenylphosphine, a toluene solution of diethyl azodicarboxylate, and THF was stirred at 0° C. for 15 hours to yield 6,6-dimethyl-1-[(2-nitrophenyl)sulfonyl]-1,4-diazepan-5-one. A mixture of this compound, 4-methylbenzenethiol, potassium carbonate, and acetonitrile was stirred at ambient temperature for 3 hours to yield 6,6-dimethyl-1,4-diazepan-5-one.

Sources & evidence

ORD record
ord-b480b3ca459d45ca85c67f51c30eda3d
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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