Sodium Hydroxide → HCID 68439348, compound

HRID 1437307Notes

Reaction equation

HRID 1437307 reaction equation
[OH-].[Na+].C[O:4][C:5]([C@@H:7]1[CH2:12][O:11][CH2:10][CH2:9][N:8]1[C:13]([C:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N:17]([C:26]2[CH:27]=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[N:16]=1)=[O:14])=[O:6]>O1CCCC1>[CH3:33][O:32][C:29]1[N:28]=[CH:27][C:26]([N:17]2[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:19][C:15]([C:13]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][C@H:7]3[C:5]([OH:6])=[O:4])=[O:14])=[N:16]2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68437459HCID 68437459, compound

Product 1

HCID 68439348HCID 68439348, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1N Aqueous solution of sodium hydroxide (3 mL) was added dropwise to the above-obtained (3S)-4-[1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)pyrazole-3-carbonyl]morpholine-3-carboxylic acid methyl ester (387 mg) in tetrahydrofuran (5 mL) with ice cooling, followed by stirring at room temperature for 3 hours. The reaction mixture was partitioned between 1N aqueous solution of hydrochloric acid (3.5 mL) and chloroform. Subsequently, the organic layer was dried over sodium sulfate anhydrate. The mixture was subjected to filtration, and the solvent was removed under reduced pressure, to thereby give (3S)-4-[1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)pyrazole-3-carbonyl]morpholine-3-carboxylic acid as an amorphous product (338 mg, 90%).

Workup

  1. customThe reaction mixture was partitioned between 1N aqueous solution of hydrochloric acid (3.5 mL) and chloroform
  2. dry with materialSubsequently, the organic layer was dried over sodium sulfate anhydrate
  3. filtrationThe mixture was subjected to filtration
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-05525178bccc42c38ac9bc71257fd4e7
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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