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

HRID 1908261Notes

Reaction equation

HRID 1908261 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-b1b7b62e605c419f9065910838057865
Source dataset
uspto-grants-2013_12
Patent number
US08598211B2

Reaction notes

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