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

HRID 43624

反応式

HRID 43624 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-0bdf1f99cf0e4050beeb0918ff0f4a0d
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

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