Potassium Carbonate → HCID 68278228, compound

HRID 931522Notes

Reaction equation

HRID 931522 reaction equation
[C:1]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][C:24]1[N:25]=[C:26]([C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)[O:27][C:28]=1[CH3:29]>CN(C)C=O>[C:12]([O:11][C:1](=[O:10])[CH:2]([C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[CH2:23][C:24]1[N:25]=[C:26]([C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)[O:27][C:28]=1[CH3:29])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68324Di-tert-butyl malonateHCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate

Product 1

HCID 68278228HCID 68278228, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

A mixture of di-tert-butyl malonate (4.3 g, 19.91 mmol, 1.99 equiv) and potassium carbonate (2.8 g, 20.29 mmol, 2.03 equiv) in N,N-dimethylformamide (30 mL) was stirred at 65° C. for 30 min. A solution of methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate (2.65 g, 10.00 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL) was then added dropwise with stirring to the reaction mixture. The resulting solution was stirred at 65° C. overnight and then quenched with 60 mL of ice and water. The mixture was extracted with 2×50 mL of ethyl acetate. The combined organic layers was washed with 3×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 4.0 g (90%) of methyl 4-(4-(3-tert-butoxy-2-(tert-butoxycarbonyl)-3-oxopropyl)-5-methyloxazol-2-yl)benzoate as a light yellow solid. LC-MS: (ES, m/z): 446 [M+H]+, 390, 334, 272, 230, 115.

Workup

  1. stirringwith stirring to the reaction mixture
  2. stirringThe resulting solution was stirred at 65° C. overnight
  3. customquenched with 60 mL of ice and water
  4. extractionThe mixture was extracted with 2×50 mL of ethyl acetate
  5. washThe combined organic layers was washed with 3×30 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7f9ece93f29a49459d10bff54a4d0c66
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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