Sodium Hydroxide → HCID 69195542, compound

HRID 1370268Notes

Reaction equation

HRID 1370268 reaction equation
[OH-].[Na+].C([O:6][C@H:7]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([CH:23]2[O:27][N:26]=[C:25]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[CH2:24]2)=[O:22])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)C>CO.C1COCC1>[OH:6][CH:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:15]=[CH:16][C:17]([NH:20][C:21]([C@H:23]2[O:27][N:26]=[C:25]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[CH2:24]2)=[O:22])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69195208HCID 69195208, compound

Product 1

HCID 69195542HCID 69195542, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

) NaOH 1N (1 ml) was added dropwise to a stirred solution of (S)-[4-[[[4,5-dihydro-3-(3-pyridinyl)-5-isoxazolyl]carbonyl]amino]phenyl]phenylmethyl acetate (0.001 mol) in methanol (20 ml) and THF (20 ml) and the reaction mixture was stirred for one hour at RT. The solvent was evaporated under reduced pressure. The white solid residue was taken up into methanol. The precipitate was filtered off, washed with methanol and diethyl ether, then dried, yielding 0.2 g (92%) of (S)-4,5-dihydro-N-[4-(hydroxyphenylmethyl)phenyl]-3-(3-pyridinyl)-5-isoxazolecarboxamide (compound 57).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. filtrationThe precipitate was filtered off
  3. washwashed with methanol and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-6a970065beba4d6b9522e92aad6bae62
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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