Acetone → HCID 69513230, compound

HRID 1593490Notes

Reaction equation

HRID 1593490 reaction equation
[CH3:1][N:2]([CH:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1)[C:3]([C:5]1[S:6][C:7]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C:21](=NOC)[CH2:20][CH2:19]3)=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:9]=1)=[O:4].[O:35]1CCOCC1.CC(C)=O>Cl>[CH3:1][N:2]([CH:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1)[C:3]([C:5]1[S:6][C:7]([C:16]2[CH:17]=[C:21]3[C:22](=[CH:23][CH:24]=2)[C:18](=[O:35])[CH2:19][CH2:20]3)=[C:8]([C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 312751,4-DioxaneHCID 86760577HCID 86760577, compound

Product 1

HCID 69513230HCID 69513230, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The product of step 3 (476 mg 1 mmol) was dissolved in 5N hydrochloric acid (10 ml), dioxane (10 ml) and acetone (5 ml) and heated at 80° C. for 2 hours. The resulting solution was concentrated in vacuo and co-evaporated with ethanol (×3) to afford a crude solid. This was partitioned between saturated sodium bicarbonate solution and ethyl acetate. The aqueous phase was re-extracted with ethyl acetate (×2), and the combined organic extracts were washed with water (×3), brine, dried and evaporated in vacuo to a crude solid. This was purified by column chromatography (1:9:40 0.880 ammonia:thanol:dichloromethane) to afford title product (300 mg, 67%); MS (AP+) m/e 446 [M+H]+

Workup

  1. concentrationThe resulting solution was concentrated in vacuo and co-evaporated with ethanol (×3)
  2. customto afford a crude solid
  3. customThis was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  4. extractionThe aqueous phase was re-extracted with ethyl acetate (×2)
  5. washthe combined organic extracts were washed with water (×3), brine
  6. customdried
  7. customevaporated in vacuo to a crude solid
  8. customThis was purified by column chromatography (1:9:40 0.880 ammonia:thanol:dichloromethane)

Sources & evidence

ORD record
ord-67dcc6486a614cbc9c0356463e531536
Source dataset
uspto-grants-2007_11
Patent number
US07297693B2

Reaction notes

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