Water → Acetic acid 3-(4-{[(4-chloro-benzenesulfonyl)-(2-oxo-azepan-3-yl)-amino]-methyl}-phenyl)-[1,2,4]oxadiazol-5-ylmethyl ester

HRID 851999Notes

Reaction equation

HRID 851999 reaction equation
[C:1]([O:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]([CH2:40][C:41]2[CH:50]=[CH:49][C:44]([C:45]([NH:47]O)=[NH:46])=[CH:43][CH:42]=2)[CH:32]2[CH2:38][CH2:37][CH2:36][CH2:35][NH:34][C:33]2=[O:39])(=[O:30])=[O:29])=[CH:24][CH:23]=1.O>CN(C)C=O>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:31]([CH2:40][C:41]2[CH:42]=[CH:43][C:44]([C:45]3[N:46]=[C:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[O:8][N:47]=3)=[CH:49][CH:50]=2)[CH:32]2[CH2:38][CH2:37][CH2:36][CH2:35][NH:34][C:33]2=[O:39])(=[O:29])=[O:30])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 83766Acetoxyacetic acidHCID 178513311HCID 178513311, compound

Product 1

HCID 69489530Acetic acid 3-(4-{[(4-chloro-benzenesulfonyl)-(2-oxo-azepan-3-yl)-amino]-methyl}-phenyl)-[1,2,4]oxadiazol-5-ylmethyl esterYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of acetoxyacetic acid (0.13 g, 1.10 mmol) in 5 ml dimethylformamide were added 1,1′-carbonyl-diimidazole (0.18 g, 1.10 mmol). The mixture was stirred at room temperature for 10 minutes, heated to 40° C. for a few minutes and cooled to room temperature. 4-{[(4-Chloro-benzenesulfonyl)-(2-oxo-azepan-3-yl)-amino]-methyl}-N-hydroxy-benzamidine (0.45 g, 1.00 mmol) was added and the mixture was stirred at 100° C. for 5 hours and then poured into water. Filtration and chromatography on silicagel with ethylacetate/heptane (3/1) yielded 0.15 g (29%) acetic acid 3-(4-{[(4-chloro-benzenesulfonyl)-(2-oxo-azepan-3-yl)-amino]-methyl}-phenyl)-[1,2,4]oxadiazol-5-ylmethyl ester as white solid, MS: m/e (%)=533.0 (MH+, 100).

Workup

  1. temperatureheated to 40° C. for a few minutes
  2. temperaturecooled to room temperature
  3. stirringthe mixture was stirred at 100° C. for 5 hours
  4. filtrationFiltration and chromatography on silicagel with ethylacetate/heptane (3/1)

Sources & evidence

ORD record
ord-36e9b8e265c84d5da7fb76684784fa86
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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