Citric Acid → HCID 71203162, compound

HRID 633619Notes

Reaction equation

HRID 633619 reaction equation
[F:1][C:2]([F:7])([F:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].CS([C:14]1[N:15]=[C:16]([CH2:40][CH2:41][CH3:42])[C:17]2[N:22]=[C:21]([C:23]3[CH:37]=[C:36]([CH3:38])[C:26]([O:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[C:25]([CH3:39])[CH:24]=3)[O:20][C:18]=2[N:19]=1)(=O)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:38][C:36]1[CH:37]=[C:23]([C:21]2[O:20][C:18]3[N:19]=[C:14]([O:5][CH2:4][CH2:3][C:2]([F:7])([F:6])[F:1])[N:15]=[C:16]([CH2:40][CH2:41][CH3:42])[C:17]=3[N:22]=2)[CH:24]=[C:25]([CH3:39])[C:26]=1[O:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 1375123,3,3-Trifluoro-1-propanolHCID 71186232HCID 71186232, compound

Product 1

HCID 71203162HCID 71203162, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

116 mg of 3,3,3-trifluoropropan-1-ol were added to 46 mg of sodium hydride (60% pure in mineral oil) in 1.5 ml of dry N,N-dimethylformamide. After 5 min, 111 mg of tert-butyl [4-(5-methanesulfonyl-7-propyloxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate were added, and the reaction was stirred initially at room temperature for 2 h and then at 80° C. for 15 min. For work-up, saturated aqueous citric acid solution was added, and the reaction was extracted three times with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by preparative HPLC gave 12 mg (10%) of the title compound.

Workup

  1. waitat 80° C. for 15 min
  2. extractionthe reaction was extracted three times with ethyl acetate
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-cb626f5058fe4bd7901cb3ee91cec591
Source dataset
uspto-grants-2016_04
Patent number
US09321787B2

Reaction notes

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