N-(1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine Benzylester → N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine

HRID 1906628

반응식

HRID 1906628 반응식
C([O:8][C:9](=[O:27])[C@H:10]([CH3:26])[NH:11][CH:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.[H][H]>C(O)C.C(O)(=O)C.[Pd]>[CH2:24]([O:23][C:21]([CH:12]([NH:11][C@H:10]([C:9]([OH:27])=[O:8])[CH3:26])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:22])[CH3:25]

참가 물질

6

반응물 2

HCID 13345971N-(1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine BenzylesterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 13044262N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

N-(1-Ethoxycarbonyl-3-Phenylpropyl)-L-Alanine Benzylester (4.2 g) is dissolved in 40 ml ethanol, to which is added 630 mg 10% Pd-C and a few drops of acetic acid. Hydrogenation occurs under a 30 psi hydrogen atmosphere at room temperature overnight. The resulting mixture is filtered through celite and dried under vacuum to remove the solvent, yielding a residue. The residue is partitioned between chloroform and aqueous 5% NaHCO3, separated, and the chloroform layer further washed with aqueous 5% NaHCO3. The aqueous layers are combined, acidified to pH 3.5 with dilute HCl, extracted with chloroform or ethylacetate several times, dried over MgSO4, and placed under vacuum to evaporate the solvent and yield 2.5 g of the diastereoisomeric product, a brown sticky solid [TLC (Silica gel; CHCl3 /MeOH/HOAC=9:1:0.5); Rf=0.4].

후처리

  1. filtrationThe resulting mixture is filtered through celite
  2. customdried under vacuum
  3. customto remove the solvent
  4. customyielding a residue
  5. customThe residue is partitioned between chloroform and aqueous 5% NaHCO3
  6. customseparated
  7. washthe chloroform layer further washed with aqueous 5% NaHCO3
  8. extractionextracted with chloroform or ethylacetate several times
  9. dry with materialdried over MgSO4
  10. customto evaporate the solvent and yield 2.5 g of the diastereoisomeric product

출처 및 근거

ORD 기록
ord-b0927fd42b5647caac7d9bc33a5eef9a
출처 데이터셋
uspto-grants-1987_03
특허 번호
US04652668

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