Water → HCID 66638711, compound

HRID 1094451Notes

Reaction equation

HRID 1094451 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[F:29])[C:10](=[O:21])[CH2:11][C:12]1[N:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O.OS([O-])(=O)=O.[Na+]>CCO>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[F:29])[CH:10]([OH:21])[CH2:11][C:12]1[N:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 516919Sodium BisulfateHCID 4311764Sodium borohydrideHCID 66639334HCID 66639334, compound

Product 1

HCID 66638711HCID 66638711, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[3-tert-butoxycarbonylamino-4-(2-fluoro-phenyl)-2-oxo-butyl]-nicotinic acid (14 g, 35 mmol) in 100 mL of EtOH at 0° C. is added NaBH4 (5.3 g, 140 mmol). After 20 min, 30 mL of water is added to the reaction and the reaction poured into 300 ml of water. The pH is adjusted to ˜pH3 with 2M NaHSO4 at which point a white solid precipitates and isolation by filtration gives the title compound.

Workup

  1. customprecipitates
  2. filtrationisolation by filtration

Sources & evidence

ORD record
ord-951969ef54ea4c0ebebbdf647a5cb058
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

Loading…