Diethyl Ether → HCID 67245049, compound

HRID 2239731Notes

Reaction equation

HRID 2239731 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16])=[O:7].[C:17]([N:21]1[C:25](=[O:26])[C:24](Cl)=[C:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[S:22]1(=[O:35])=[O:34])([CH3:20])([CH3:19])[CH3:18].C(OCC)C>CC#N.CN(C=O)C>[C:17]([N:21]1[C:25](=[O:26])[C:24]([NH:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:16])=[O:7])=[C:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[S:22]1(=[O:34])=[O:35])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxideHCID 67242907HCID 67242907, compound

Product 1

HCID 67245049HCID 67245049, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

2,6-Dimethylphenyl 4-aminobutanoate hydrochloride (80.4 mg, 0.33 mmol) and 2-tert-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (89.9 mg, 0.91 mmol) were dissolved in a mixture of MeCN/DMF (4:1, 5 ml, dry). TEA (0.134 ml) was added and the reaction mixture was stirred at rt for 15 h. Diethyl ether (30 ml) was added and the resulting mixture was extracted with water (2×10 ml). The organic layer was dried (MgSO4), evaporated and the residue was purified by column chromatography on silica, using n-heptane/EtOAc (7:3) as eluent. The obtained product was further purified by re-chromatography, using the same conditions as before, to give the title compound (17 mg, 11%) as colorless oil, which solidified upon standing. 1H NMR (400 MHz, CDCl3): δ 1.73 (s, 9H), 1.78-1.85 (m, 2H), 2.06 (s, 6H), 2.38 (t, 2H), 2.96-3.01 (m, 2H), 5.37 (bt, 1H), 7.04 (s, 31), 7.42-7.44 (m, 3H), 7.50-7.52 (m, 2H).

Workup

  1. extractionthe resulting mixture was extracted with water (2×10 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customthe residue was purified by column chromatography on silica
  5. customThe obtained product was further purified by re-chromatography

Sources & evidence

ORD record
ord-597fefaab9f648e999ed4fd631fad0e7
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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