Methanol → 3-(2-(3-(4-Fluorophenyl)-1H-pyrazol-1-yl)nicotinamido)-2-hydroxy-4-phenylbutanoic acid

HRID 2170871Notes

Reaction equation

HRID 2170871 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[N:36]=[CH:35][CH:34]=[CH:33][C:14]=3[C:15]([NH:17][CH:18]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:19]([OH:25])[C:20]([O:22]CC)=[O:21])=[O:16])[N:9]=2)=[CH:4][CH:3]=1.O1CCCC1.C(Cl)Cl.CO>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[N:36]=[CH:35][CH:34]=[CH:33][C:14]=3[C:15]([NH:17][CH:18]([CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:19]([OH:25])[C:20]([OH:22])=[O:21])=[O:16])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 67239028Ethyl 3-(2-(3-(4-fluorophenyl)-1H-pyrazol-1-yl)nicotinamido)-2-hydroxy-4-phenylbutanoate

Product 1

HCID 672393523-(2-(3-(4-Fluorophenyl)-1H-pyrazol-1-yl)nicotinamido)-2-hydroxy-4-phenylbutanoic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of ethyl 3-(2-(3-(4-fluorophenyl)-1H-pyrazol-1-yl)nicotinamido)-2-hydroxy-4-phenylbutanoate (4500 mg, 9.21 mmol) in tetrahydrofuran (THF) (500 ml) lithium hydroxide (LiOH) (441 mg, 18.42 mmol) in water (100 ml) was added, and the mixture stirred for 2 h at room temperature. After completion of the reaction (tlc: CH2Cl2+10% (v/v) methanol) the mixture was concentrated under reduced pressure and after addition of water (300 ml) acidified using 2 n HCl. The precipitate formed was filtered off and dried to give 4.13 g of a white amorphous solid.

Workup

  1. additionwas added
  2. concentrationwas concentrated under reduced pressure
  3. additionafter addition of water (300 ml)
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. customdried

Sources & evidence

ORD record
ord-c753ee0ebaa54e6abdf5d43bd3961231
Source dataset
uspto-grants-2015_06
Patent number
US09051304B2

Reaction notes

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