Hydrochloric Acid → Ethyl 2-methyl-3-acetylamino-4-methoxycarbonyl-5-oxohexanoate

HRID 487760Notes

Reaction equation

HRID 487760 reaction equation
[C:1]([NH:4][C@@H:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH3:15])[O:8][C:7]([O:19]CC)([O:16][CH2:17][CH3:18])[C@H:6]1[CH3:22])(=[O:3])[CH3:2].O.Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:22][CH:6]([CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]([C:11]([O:13][CH3:14])=[O:12])[C:9](=[O:8])[CH3:15])[C:7]([O:16][CH2:17][CH3:18])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 67850473methyl trans-4-acetylamino-2,2-diethoxy-3,6-dimethyl-3,4-dihydro-2H-pyran-5-carboxylate

Product 1

HCID 14167791Ethyl 2-methyl-3-acetylamino-4-methoxycarbonyl-5-oxohexanoateYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl trans-4-acetylamino-2,2-diethoxy-3,6-dimethyl-3,4-dihydro-2H-pyran-5-carboxylate (12.2 g) (Example 6) in 200 ml tetrahydrofuran was added 3.0 ml water and 1.0 ml 1N HCl. The mixture was stirred at 20°-25° C. for 16 hours, then neutralized by adding 1.0 g anhydrous potassium carbonate. The mixture was filtered and the filtrate evaporated at reduced pressure to give 11.4 g of crude product which was crystallised from toluene/hexane (50:50) giving ethyl 2-methyl-3-acetylamino-4-methoxycarbonyl-5-oxohexanoate (6.8 g), m.p. 93°-6° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated at reduced pressure
  3. customto give 11.4 g of crude product which
  4. customwas crystallised from toluene/hexane (50:50)

Sources & evidence

ORD record
ord-a5f071f4df994b30a389937cdd885f21
Source dataset
uspto-grants-1994_03
Patent number
US05296613

Reaction notes

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