Diethyl Ether → HCID 67245049, compound

HRID 2422133Notes

Reaction equation

HRID 2422133 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-eedb3fab5f2943f48de52952df0819e6
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

Loading…