Trans-2,2-diethoxy-3,6-dimethyl-4-acetylamino-5-(4'-chlorophenylcarbamoyl)-3,4-dihydro-2H-pyran → Ethyl 2-methyl-3-acetylamino-4-(4'-chlorophenylcarbamoyl)-5-oxohexanoate

HRID 487761Notes

Reaction equation

HRID 487761 reaction equation
[CH2:1]([O:3][C:4]1([O:26]CC)[C@@H:9]([CH3:10])[C@H:8]([NH:11][C:12](=[O:14])[CH3:13])[C:7]([C:15](=[O:24])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:6]([CH3:25])[O:5]1)[CH3:2]>O1CCCC1.Cl.O>[CH3:10][CH:9]([CH:8]([NH:11][C:12](=[O:14])[CH3:13])[CH:7]([C:15](=[O:24])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:6](=[O:5])[CH3:25])[C:4]([O:3][CH2:1][CH3:2])=[O:26]

Participants

5

Reactant 1

HCID 86746202Trans-2,2-diethoxy-3,6-dimethyl-4-acetylamino-5-(4'-chlorophenylcarbamoyl)-3,4-dihydro-2H-pyran

Product 1

HCID 14167793Ethyl 2-methyl-3-acetylamino-4-(4'-chlorophenylcarbamoyl)-5-oxohexanoate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Trans-2,2-diethoxy-3,6-dimethyl-4-acetylamino-5-(4'-chlorophenylcarbamoyl)-3,4-dihydro-2H-pyran (76.5 g) (Example 18) was stirred at room temperature in a mixture of tetrahydrofuran (200 ml) and 1N hydrochloric acid (10 ml) for 16 hours. The reaction mixture was diluted with water, extracted with ethyl acetate and the organic extract dried in anhydrous magnesium sulphate and evaporated to dryness. The residual solid was triturated with diethyl ether to give ethyl 2-methyl-3-acetylamino-4-(4'-chlorophenylcarbamoyl)-5-oxohexanoate, 66 g, m.p. 169°-73° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionthe organic extract
  3. dry with materialdried in anhydrous magnesium sulphate
  4. customevaporated to dryness
  5. customThe residual solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-92b81fa0d9ce46a8bbed43f21334972e
Source dataset
uspto-grants-1994_03
Patent number
US05296613

Reaction notes

Loading…