Sodium Hydroxide → HCID 66620465, compound

HRID 415158Notes

Reaction equation

HRID 415158 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]2[CH2:26][CH2:25][CH2:24][N:23]2C([O-])=O)[CH:5]=[CH:6][C:7]=1[C:8](=O)[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18]C)=[O:17])[C:11]=1[OH:20].[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]([CH:22]2[CH2:26][CH2:25][CH2:24][NH:23]2)[CH:5]=[CH:6][C:7]=1[C:8]1[O:20][C:11]2[C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86633087HCID 86633087, compound

Product 1

HCID 66620465HCID 66620465, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

The mixture of polyphosphoric acid (4 g) and 2-(3-fluoro-4-(2-hydroxy-3-(methoxycarbonyl)phenylcarbamyl)phenyl)pyrrolidine-1-carboxylate (1.1 g, 2.23 mmol) was stirred at 180° C. for 0.5 h under nitrogen, and then cooled to 0° C. Water (50 mL) was added to the mixture and adjusted to pH=7 with sodium hydroxide at 0° C., the solution was extracted with ethyl acetate; the liquid layer was adjusted to pH=5, the water was evaporated under vacuum, the methanol was added, filtered, the solvent was dried over anhydrous sodium sulfate, evaporated to obtain 2-(2-fluoro-4-(pyrrolidin-2-yl)phenyl)benzo[d]oxazole-7-carboxylic acid (500 mg, yield 69%). LC-MS (ESI) m/z: 327 (M+1)+.

Workup

  1. temperaturecooled to 0° C
  2. extractionthe solution was extracted with ethyl acetate
  3. customthe water was evaporated under vacuum
  4. additionthe methanol was added
  5. filtrationfiltered
  6. dry with materialthe solvent was dried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-c0f0c0699d504711aea5b319eb02c792
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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