Potassium Carbonate → HCID 462652, compound

HRID 1080896Notes

Reaction equation

HRID 1080896 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[S:7][S:8][C:9]([CH2:12][O:13][Si](C(C)(C)C)(C)C)=[CH:10][CH:11]=1)(=[O:3])[CH3:2].F.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([NH:4][CH2:5][C:6]1[S:7][S:8][C:9]([CH2:12][OH:13])=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14917Hydrofluoric AcidHCID 11724284HCID 11724284, compound

Product 1

HCID 462652HCID 462652, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of 52 mg (0.152 mmol) of the (silyloxy)amide 19 in 1.0 mL of acetonitrile, previously cooled in an ice-water bath, was added 500 μL of a 1:3 solution of 30% aqueous hydrofluoric acid solution in acetonitrile. The resulting solution was stirred for 15 minutes in the ice bath, after which time TLC analysis showed the reaction to be complete. The acid was neutralized by cautious addition of about 15 mL of a 10% aqueous potassium carbonate solution to the reaction mixture. The reaction mixture was partitioned between 20 mL of water and 40 mL of ethyl acetate. The layers were separated and the aqueous phase was extracted with 40 mL of ethyl acetate. The combined organic phases were washed with two 50-mL portions of saturated aqueous sodium chloride, dried (Na2SO4) and concentrated in vacuo. The residue (33 mg) was chromatographed over 20 g of silica gel (ethyl acetate) to give 24 mg (71%) of acetamide 20 as an orange oil. 1H NMR (CDCl3) δ6.792 (m, 2H, C=CH; minor isomer), 6.309 (d, J=6.4 Hz, 1H, C=CH; major isomer), 6.269 (d, J=5.6 Hz, 1H, C=CH; major isomer), 6.82 (br s, 1H, NH), 4.276 (br s, 2H, CH2O; minor isomer), 4.512 (d, J=5.6 Hz, 2H, CH2N; minor isomer), 4.228 (br s, 2H, CH2 0; major isomer), 4.023 (d, J=6.0 Hz, 2H, CH2N; major isomer), 2.05 (s, 1H, OH), 1.998 (s, 3H, COCH3 ; major isomer); 13C NMR (CDCl3) δ170.116, 144.100 (minor isomer), 141.214 (minor isomer), 134.827 (major isomer), 132.384 (major isomer), 126.528 (major isomer), 125.815 (minor isomer), 125.254 (minor isomer), 125.178 (major isomer), 64.499 (major isomer), 60.099 (minor isomer), 43.690 (major isomer), 38.631 (minor isomer), 23.140 (major isomer), 21.011 (minor isomer); MS (LSIMS) m/z=57 (100%), 217 (M+).

Workup

  1. customthe reaction
  2. customThe reaction mixture was partitioned between 20 mL of water and 40 mL of ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with 40 mL of ethyl acetate
  5. washThe combined organic phases were washed with two 50-mL portions of saturated aqueous sodium chloride
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue (33 mg) was chromatographed over 20 g of silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-847f9992752a4693be94fa4742bdd928
Source dataset
uspto-grants-1996_12
Patent number
US05583235

Reaction notes

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