Triethylsilane → 2-oxo-3,6-dimethyl-4-acetylamino-5-(4'-chlorophenylcarbamoyl)-3,4,5,6-tetrahydro-2H-pyran

HRID 466285Notes

Reaction equation

HRID 466285 reaction equation
[CH3:1][CH:2]([CH:8]([NH:23][C:24](=[O:26])[CH3:25])[CH:9]([C:13](=[O:22])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:10](=[O:12])[CH3:11])[C:3](OCC)=[O:4].C([SiH](CC)CC)C>FC(F)(F)C(O)=O.C(OCC)C>[O:4]=[C:3]1[CH:2]([CH3:1])[CH:8]([NH:23][C:24](=[O:26])[CH3:25])[CH:9]([C:13](=[O:22])[NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:10]([CH3:11])[O:12]1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 14167793Ethyl 2-methyl-3-acetylamino-4-(4'-chlorophenylcarbamoyl)-5-oxohexanoate

Product 1

HCID 141678112-oxo-3,6-dimethyl-4-acetylamino-5-(4'-chlorophenylcarbamoyl)-3,4,5,6-tetrahydro-2H-pyranYield 64%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Ethyl 2-methyl-3-acetylamino-4-(4'-chlorophenylcarbamoyl)-5-oxohexanoate (Example 25) (12 g) was dissolved in trifluoroacetic acid (50 ml), treated with triethylsilane (7.5 ml) and stirred at room temperature for 40 hours. The reaction mixture was diluted with diethyl ether and filtered. The solid was warmed with ethyl acetate then cooled and filtered to give 2-oxo-3,6-dimethyl-4-acetylamino-5-(4'-chlorophenylcarbamoyl)-3,4,5,6-tetrahydro-2H-pyran (ttt isomer) (6.8 g) m.p. 280° C. decomp.

Workup

  1. filtrationfiltered
  2. temperatureThe solid was warmed with ethyl acetate
  3. temperaturethen cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-f869ddfb2dd948579c8e16cbd8d48191
Source dataset
uspto-grants-1992_10
Patent number
US05155236

Reaction notes

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