Hydrochloric Acid → Ethyl 9-(2,3-Dichlorophenyl)-1,1-dioxo-2,3,4,5,6,9-hexahydro-7-methylpyrido-[2,3-f][1,4]thiazepine-8-carboxylate

HRID 1461475Notes

Reaction equation

HRID 1461475 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:19]2[S:18](=[O:21])(=[O:20])[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:13]=2[NH:12][C:11]([CH3:29])=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].Cl.[OH-].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:19]2[S:18](=[O:20])(=[O:21])[CH2:17][CH2:16][NH:15][CH2:14][C:13]=2[NH:12][C:11]([CH3:29])=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15035858HCID 15035858, compound

Product 1

HCID 15035859Ethyl 9-(2,3-Dichlorophenyl)-1,1-dioxo-2,3,4,5,6,9-hexahydro-7-methylpyrido-[2,3-f][1,4]thiazepine-8-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 9-(2,3-dichlorophenyl)-4-(t-butyloxycarbonyl)-1,1-dioxo-2,3,4,5,6,9-hexahydro-7-methylpyrido[2,3-f][1,4]thiazepine-8-carboxylate (2.45 g, 4.6 mmole) from Example 7, in ethyl acetate (150 mL) was cooled to 0° C. and saturated with gaseous hydrogen chloride. The mixture was warmed to room temperature. The reaction was then again chilled to 0° C. and shaken with 200 mL of cold 4 N NaOH. The aqueous layer was separated and extracted with 2×100 mL of chloroform. The ethyl acetate layer was dried with brine and the combined organic extracts were dried over Na2SO4. The solvents were evaporated under reduced pressure and the residue triturated with ether to give the product (1.86 g, 94% yield).

Workup

  1. temperatureThe reaction was then again chilled to 0° C.
  2. customThe aqueous layer was separated
  3. extractionextracted with 2×100 mL of chloroform
  4. dry with materialThe ethyl acetate layer was dried with brine
  5. dry with materialthe combined organic extracts were dried over Na2SO4
  6. customThe solvents were evaporated under reduced pressure
  7. customthe residue triturated with ether

Sources & evidence

ORD record
ord-fb2420e71e6149429b9917273ee2bf1a
Source dataset
uspto-grants-1991_12
Patent number
US05075440

Reaction notes

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