Hydrochloric Acid → {6-(Ethoxycarbonyl)-2-[3-(4-methoxyphenyl)propyl]-3-oxo-2,3-dihydro-4H-1,4-benzothiazin-4-yl}acetic acid

HRID 1360206Notes

Reaction equation

HRID 1360206 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=[CH:17][C:12]=2[S:11][CH:10]([CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:9]1=[O:34])(C)(C)C.CSC.Cl>ClCCl>[CH2:21]([O:20][C:18]([C:15]1[CH:16]=[CH:17][C:12]2[S:11][CH:10]([CH2:23][CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)[C:9](=[O:34])[N:8]([CH2:7][C:6]([OH:35])=[O:5])[C:13]=2[CH:14]=1)=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 23157958ethyl 4-(2-tert-butoxy-2-oxoethyl)-2-[3-(4-methoxyphenyl)propyl]-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate

Product 1

HCID 23157938{6-(Ethoxycarbonyl)-2-[3-(4-methoxyphenyl)propyl]-3-oxo-2,3-dihydro-4H-1,4-benzothiazin-4-yl}acetic acidYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, a boron trifluoride-diethyl ether complex (26.6 ml) was added dropwise to a solution of ethyl 4-(2-tert-butoxy-2-oxoethyl)-2-[3-(4-methoxyphenyl)propyl]-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate (13.16 g) and dimethyl sulfide (26.3 ml) in dichloromethane (250 ml). The resulting mixture was slowly warmed up to room temperature and then stirred overnight. The mixture was poured into a 1N aqueous hydrochloric acid solution and extracted with chloroform. The oil layer was washed twice with a 1N aqueous hydrochloric acid solution, dehydrated over anhydrous sodium sulfate and then concentrated under reduced pressure. {6-(Ethoxycarbonyl)-2-[3-(4-methoxyphenyl)propyl]-3-oxo-2,3-dihydro-4H-1,4-benzothiazin-4-yl}acetic acid (10.64 g) was obtained as a yellow oil.

Workup

  1. temperatureUnder ice-cooling
  2. extractionextracted with chloroform
  3. washThe oil layer was washed twice with a 1N aqueous hydrochloric acid solution
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3374f366bef46768cbceea76243192f
Source dataset
uspto-grants-2011_02
Patent number
US07879843B2

Reaction notes

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