Water → HCID 68457984, compound

HRID 501779Notes

Reaction equation

HRID 501779 reaction equation
[CH:1]1([O:6][C:7]2[CH:40]=[CH:39][C:10]([C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:24][CH2:25][C:26]4[CH:38]=[CH:37][C:29]5[C:30]([O:33][CH2:34][O:35][CH3:36])=[N:31][O:32][C:28]=5[CH:27]=4)=[C:17]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:18]=3)=[O:12])=[C:9]([OH:41])[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:48]([O:54][CH2:55]Cl)(=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50].O>CN(C)C=O.C(OCC)(=O)C>[C:48]([O:54][CH2:55][O:22][C:21](=[O:23])[CH2:20][CH2:19][C:17]1[CH:18]=[C:13]([C:11](=[O:12])[C:10]2[CH:39]=[CH:40][C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:8][C:9]=2[OH:41])[CH:14]=[CH:15][C:16]=1[O:24][CH2:25][C:26]1[CH:38]=[CH:37][C:29]2[C:30]([O:33][CH2:34][O:35][CH3:36])=[N:31][O:32][C:28]=2[CH:27]=1)(=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 68460260HCID 68460260, compound

Product 1

HCID 68457984HCID 68457984, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

1.04 g of 3-(5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-{[3-(methoxymethoxy)-1,2-benzisoxazol-6-yl]methoxy}phenyl) propanoic acid and 512 mg of potassium carbonate were suspended in 10 mL of N,N-dimethylformamide, to which 0.29 mL of chloromethyl pivalate was added, and this mixture was stirred for 2 hours at 40° C. Then, water and ethyl acetate were added to the reaction mixture, and the organic phase was separated therefrom. The remaining aqueous phase was extracted with ethyl acetate, and organic phases were combined together. After the resultant organic phase was washed with a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1] to yield 1.02 g of {[3-(5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-{[3-(methoxymethoxy)-1,2-benzisoxazol-6-yl]methoxy}phenyl) propanoyl]oxy}methyl pivalate as light yellow oil.

Workup

  1. additionwas added
  2. customthe organic phase was separated
  3. extractionThe remaining aqueous phase was extracted with ethyl acetate, and organic phases
  4. washAfter the resultant organic phase was washed with a saturated sodium chloride solution
  5. dry with materialthe washed phase was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled out under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1]

Sources & evidence

ORD record
ord-2136b8a563c54cfea333ebf62cf0ba6c
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

Loading…