Methyl 2-((benzoylamino)methyl)-3-oxobutanoate → Methyl 2-(benzamidomethyl)-3-hydroxybutanoate

HRID 1591358

반응식

HRID 1591358 반응식
[C:1]([NH:9][CH2:10][CH:11]([C:16](=[O:18])[CH3:17])[C:12]([O:14][CH3:15])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>ClCCl.CO>[C:1]([NH:9][CH2:10][CH:11]([CH:16]([OH:18])[CH3:17])[C:12]([O:14][CH3:15])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 11831808Methyl 2-((benzoylamino)methyl)-3-oxobutanoateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 19766843Methyl 2-(benzamidomethyl)-3-hydroxybutanoate수율 78%

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

Into a 200-ml stainless steel-made autoclave was placed 3.56 g (0.0143 mole) of methyl 2-benzamidomethyl-3-oxobutyrate. After nitrogen replacement, 7 ml of a separately prepared dichloromethane/methanol (7/1 by volume) mixed solvent solution containing 0.01 g (0.00894 mmole) of [RuI(p-Cymene)((-)-OcH-BINAP)]I as obtained in Example 5 was added. The resulting mixture was stirred at a hydrogen pressure of 50 kg/cm2 and a temperature of 65° C. for 20 hours. After the reaction, the reaction mixture was analyzed- by high-speed liquid chromatography. As a result, it was found that 2.79 g (percent yield: 78%) of methyl 2-benzamidomethyl-3-hydroxybutyrate had been formed and that the conversion was 80%, diastereomer selectivity 91.6%, and optical percent yield 99% ee.

후처리

  1. customas obtained in Example 5
  2. additionwas added
  3. customAfter the reaction

출처 및 근거

ORD 기록
ord-9f6649b1cbc34032a1d7575ebb5261f7
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05206399

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