3-(2-Nitrophenyl)-2-oxopropanoic acid → 2-Hydroxy-3-(2-nitrophenyl)propanoic acid

HRID 4737

Reaction equation

HRID 4737 reaction equation
N1CCC[C@H]1C(O)=O.[BH4-].[Na+].[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21](=[O:25])[C:22]([OH:24])=[O:23])([O-:13])=[O:12]>O1CCCC1>[OH:25][CH:21]([CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N+:11]([O-:13])=[O:12])[C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 795833-(2-Nitrophenyl)-2-oxopropanoic acidHCID 145742L-ProlineHCID 4311764Sodium borohydride

Product 1

HCID 136517582-Hydroxy-3-(2-nitrophenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

L-(-)-proline (7.50 g., 65.1 mmol) and sodium borohydride (2.46 g., 65.1 mmol) were stirred in tetrahydrofuran under nitrogen for sixteen hours. Recrystallized o-nitrophenylpyruvic acid (14.17 g., 76.5 mmol) in tetrahydrofuran (50 ml.) was added dropwise, and the resulting solution was stirred at room temperature for six days. The solvent was evaporated and the resulting gum was stirred with 10% aqueous HCl (200 ml.) for 4.5 hours. A small amount of solid was filtered to provide nearly racemic α-hydroxy-2-nitrobenzenepropanoic acid, 1.25 g., m.p. 98°-102° C., [α]D25 -4.21° (c 2.045, EtOH).

Workup

  1. customThe solvent was evaporated
  2. stirringthe resulting gum was stirred with 10% aqueous HCl (200 ml.) for 4.5 hours
  3. filtrationA small amount of solid was filtered

Sources & evidence

ORD record
ord-bb00c855c12145619bd8ea260945dc3b
Source dataset
uspto-grants-1988_02
Patent number
US04727183

Linked notes

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