Acetic Acid → [2-(2-Chlorophenylamino)-1,1-dimethylethyl]carbamic acid t-butyl ester

HRID 1694889ノート

反応式

HRID 1694889 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([O:19][C:20](=[O:27])[NH:21][C:22]([CH3:26])([CH3:25])[CH:23]=O)([CH3:18])([CH3:17])[CH3:16].[Cl:28][C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH2:31].C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:15]([O:19][C:20](=[O:27])[NH:21][C:22]([CH3:26])([CH3:25])[CH2:23][NH:31][C:30]1[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=1[Cl:28])([CH3:18])([CH3:17])[CH3:16]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 72402-ChloroanilineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

生成物 1

HCID 66645795[2-(2-Chlorophenylamino)-1,1-dimethylethyl]carbamic acid t-butyl ester収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4.07 g of sodium triacetoxyborohydride (19.3 mmol) was added to a solution of 3.00 g of (1,1-dimethyl-2-oxoethyl)carbamic acid t-butyl ester obtained in Reference Example 3 (16.0 mmol), 2.04 g of 2-chloroaniline (16.0 mmol) and 0.92 ml of acetic acid (16.0 mmol) in methylene chloride (160 ml) under ice-cooling, and the mixture was stirred at room temperature for 16 hours. A saturated sodium bicarbonate aqueous solution was added to the reaction mixture, followed by extraction with methylene chloride. Then, the organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=5/1) to obtain 3.49 g of the title compound (yield: 73%).

後処理

  1. temperaturecooling
  2. extractionfollowed by extraction with methylene chloride
  3. washThen, the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (elution solvent:hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-3005207d3bdb4110a4dfcbeee123739e
出典データセット
uspto-grants-2012_04
特許番号
US08158790B2

反応ノート

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