Benzyl chloroformate → N-(4-{[(Benzyloxy)carbonyl]amino}-3-methylbenzoyl)threonine methyl ester

HRID 1425100노트

반응식

HRID 1425100 반응식
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([C@@H:18]([CH3:20])[OH:19])[NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([CH3:16])[CH:8]=1.[H][H].C(=O)(O)[O-].[Na+].Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>C(O)C.[Pd].C1COCC1.O>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([C@@H:18]([CH3:20])[OH:19])[NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[C:9]([CH3:16])[CH:8]=1

참가 물질

9

반응물 4

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 67548938N-(3-Methyl-4-nitrobenzoyl)threonine methyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 68406078N-(4-{[(Benzyloxy)carbonyl]amino}-3-methylbenzoyl)threonine methyl ester수율 76.1%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

10% Pd/C (1.2 g) was added to a solution of N-(3-methyl-4-nitrobenzoyl)threonine methyl ester obtained in Example (108a) (7.2 g, 24.3 mmol) in ethanol (40 mL), and the mixture was stirred in a hydrogen atmosphere at room temperature for one hour and 20 minutes. Pd/C was filtered off, and the filtrate was concentrated under reduced pressure. Water (20 mL), THF (20 mL), sodium bicarbonate (2.52 g, 30 mmol) and benzyl chloroformate (5.37 g, 30 mmol) were added to the resulting residue, and the mixture was stirred at room temperature for one hour. Following extraction with dichloromethane, the organic layer was washed with water, a 1 N aqueous hydrochloric acid solution and brine, dried over magnesium sulfate, and concentrated. Thereafter, the resulting residue was purified by silica gel column chromatography (elution solvent: chloroform/methanol=1/0, 95/5, 90/10, 85/15) to obtain 7.4 g of the title compound as a colorless solid (76%).

후처리

  1. filtrationPd/C was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionextraction with dichloromethane
  4. washthe organic layer was washed with water
  5. dry with materiala 1 N aqueous hydrochloric acid solution and brine, dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThereafter, the resulting residue was purified by silica gel column chromatography (elution solvent: chloroform/methanol=1/0, 95/5, 90/10, 85/15)

출처 및 근거

ORD 기록
ord-3dda73e21daa479a9fa3d680c91901d0
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927588B2

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