Acetic Acid → HCID 16110667, compound

HRID 2386180Notes

Reaction equation

HRID 2386180 reaction equation
[Si:1]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]([OH:29])=[O:28])=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:30]1(C)C=CC=CC=1.[Si](C=[N+]=[N-])(C)(C)C.C(O)(=O)C>CO>[O:8]([CH:9]([C:22]1[O:23][C:24]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1140TolueneHCID 167693TrimethylsilyldiazomethaneHCID 68526703HCID 68526703, compound

Product 1

HCID 16110667HCID 16110667, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(1-(tert-Butyldimethylsilyloxy)-7-phenylheptyl)oxazole-5-carboxylic acid (281 mg, 6.673 mmol) was dissolved in a mixture of MeOH:toluene (4 mL: 10 mL), cooled to 0° C. and TMSCHN2 (2 M in hexanes, 3 equiv) was added dropwise under Ar. The reaction mixture was stirred at room temperature for 0.5 h before it was cooled to 0° C. and acetic acid was added dropwise until the solution turned from yellow to clear. The mixture was evaporated in vacuo and the resulting solid was dissolved in EtOAc. The solution was washed with saturated aqueous NaHCO3, washed with saturated aqueous NaCl and dried over Na2SO4. Evaporation in vacuo yielded the crude ester which was purified by flash chromatography (10-30% EtOAc/hexanes) to afford the pure ester as a clear oil (225 mg, 78%): 1H NMR (CDCl3, 500 MHz) δ 7.78 (s, 1H), 7.36-7.33 (m, 2H), 725-7.23 (m, 3H), 4.92 (t, 1H, J=7.0 Hz), 3.98 (s, 3H), 2.67 (t, 2H, J=7.5 Hz), 2.12-1.94 (m, 2H), 1.72-1.67 (m, 2H), 1.53-1.43 (m, 6H), 0.98 (s, 9H), 0.17 (s, 3H), 0.08 (s, 3H); 13C NMR (CDCl3, 125 MHz) δ 169.0, 158.5, 143.1, 142.6, 134.5, 128.8, 128.6, 126.0, 69.1, 52.5, 36.7, 36.3, 31.8, 29.5, 26.1, 26.1, 25.4, 18.6, −4.6, −4.8.

Workup

  1. temperaturewas cooled to 0° C.
  2. customThe mixture was evaporated in vacuo
  3. dissolutionthe resulting solid was dissolved in EtOAc
  4. washThe solution was washed with saturated aqueous NaHCO3
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. customEvaporation in vacuo
  8. customyielded the crude ester which
  9. customwas purified by flash chromatography (10-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c7818d15774947f2b8df1bcfbc265a0f
Source dataset
uspto-grants-2012_09
Patent number
US08268817B2

Reaction notes

Loading…