Water → HCID 66681729, compound

HRID 1964731Notes

Reaction equation

HRID 1964731 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:34])[O:5][C:6]1[CH:7]=[C:8]([CH:20]=[C:21]([C:23]2[NH:24][C:25]([C:28]3[O:29][C@@H:30]([CH3:33])[CH2:31][N:32]=3)=[CH:26][CH:27]=2)[CH:22]=1)[O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([O:18]C)=[O:17])=[N:14][CH:15]=1.O.O.[OH-].[Li+].[Cl-].[NH4+]>CO>[CH3:1][O:2][CH2:3][C@H:4]([CH3:34])[O:5][C:6]1[CH:7]=[C:8]([CH:20]=[C:21]([C:23]2[NH:24][C:25]([C:28]3[O:29][C@@H:30]([CH3:33])[CH2:31][N:32]=3)=[CH:26][CH:27]=2)[CH:22]=1)[O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([OH:18])=[O:17])=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 66682510HCID 66682510, compound

Product 1

HCID 66681729HCID 66681729, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)pyridine-2-carboxylate (264 mg, 0.57 mmol) synthesized in Example (129e) was dissolved in methanol (20 mL), and water (3 mL) and lithium hydroxide monohydrate (71 mg, 1.70 mmol) were added, followed by stirring at 50° C. for 1 hour under nitrogen atmosphere. To the reaction solution, a saturated aqueous ammonium chloride solution (50 mL) was added, followed by extraction twice with methylene chloride (40 mL), washing with saturated brine, and drying over sodium sulfate. The solvent was distilled off under reduced pressure, and vacuum drying was carried out to afford the desired compound (256 mg, yield 100%) as a pale yellow solid.

Workup

  1. extractionfollowed by extraction twice with methylene chloride (40 mL)
  2. washwashing with saturated brine
  3. dry with materialdrying over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure, and vacuum
  5. customdrying

Sources & evidence

ORD record
ord-1b4aa4bade4d4fdb8dfca6be6bb88eb4
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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