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

HRID 4737

반응식

HRID 4737 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bb00c855c12145619bd8ea260945dc3b
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04727183

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