Tetrahydrofuran → 2-Hydroxy-4-phenyl-3-(2-(2-phenylthiazol-4-yl)nicotinamido)butanoic acid

HRID 1400232Notes

Reaction equation

HRID 1400232 reaction equation
[OH:1][CH:2]([CH:8]([NH:16][C:17](=[O:35])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][C:19]=1[C:24]1[N:25]=[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[S:27][CH:28]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5]CC)=[O:4].C1COCC1>O>[OH:1][CH:2]([CH:8]([NH:16][C:17](=[O:35])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][C:19]=1[C:24]1[N:25]=[C:26]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[S:27][CH:28]=1)[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 67540490Ethyl 2-hydroxy-4-phenyl-3-(2-(2-phenylthiazol-4-yl)nicotinamido)butanoate

Product 1

HCID 675402612-Hydroxy-4-phenyl-3-(2-(2-phenylthiazol-4-yl)nicotinamido)butanoic acidYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-hydroxy-4-phenyl-3-(2-(2-phenylthiazol-4-yl)nicotinamido)-butanoate (1.31 g, 2.69 mmol) in THF (40 ml) LiOH (0.14 g, 5.85 mmol) in water (10 ml) was added at 10° C., the mixture stirred for 1 hour at room temperature and then for 2 hours at 60° C. The mixture then was concentrated under reduced pressure, water and 3 ml of 2n HCl added, poured into 300 ml of a mixture of dichloromethane and 5% acetone. The organic layer was dried, filtered and concentrated under reduced pressure to give 1.19 g of the title acid;

Workup

  1. waitfor 2 hours at 60° C
  2. concentrationThe mixture then was concentrated under reduced pressure, water and 3 ml of 2n HCl
  3. additionadded
  4. additionpoured into 300 ml of a mixture of dichloromethane and 5% acetone
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f53ee1ae0914400bc4ebd3ed87abca7
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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