Potassium Carbonate → HCID 66917719, compound

HRID 1818001Notes

Reaction equation

HRID 1818001 reaction equation
C(OC(=O)C[O:8][C:9]1[C:14]2[N:15]([CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=3)C(=O)[O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)(C)(C)C.BrCC(OC(C)(C)C)=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CN(C=O)C>[CH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[CH2:19][NH:15][C:14]1[C:9]([OH:8])=[CH:10][CH:11]=[CH:12][C:13]=1[OH:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 66917649HCID 66917649, compound

Product 1

HCID 66917719HCID 66917719, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

Synthesis of (3-Naphthalen-2-ylmethyl-2-oxo-2,3-dihydro-benzooxazol-4-yloxy)-acetic acid tert-butyl ester, I-88. A mixture of compound I-87 (140 mg, 0.48 mmol), tert-butyl bromoacetate (136 mg, 0.7 mmol) and K2CO3 (95 mg, 0.7 mmol) in acetone (10 ml) and DMF (5 ml) was stirred at rt over night and then partitioned between EtOAc and water. Water layer was extracted with EtOAc. The combined organic phase was washed with water, brine and dried over sodium sulfate. After removal of solvent, 160 mg of compound I-88 was obtained. 1H-NMR (500 MHz, CDCl3).

Workup

  1. additionA mixture of compound
  2. custompartitioned between EtOAc and water
  3. extractionWater layer was extracted with EtOAc
  4. washThe combined organic phase was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of solvent, 160 mg of compound
  7. customwas obtained

Sources & evidence

ORD record
ord-0d1802b9566d4fd6a716d27d90cdd70f
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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