Acetic Anhydride → Tert-butyl 2-acetamido-1-(4-chlorophenyl)ethylcarbamate

HRID 423094ノート

反応式

HRID 423094 の反応式
[NH2:1][CH2:2][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.C(N(C(C)C)C(C)C)C.[C:28](OC(=O)C)(=[O:30])[CH3:29]>C1COCC1>[C:28]([NH:1][CH2:2][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:4]1[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=1)(=[O:30])[CH3:29]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 57750386tert-butyl N-[2-amino-1-(4-chlorophenyl)ethyl]carbamate2 回

生成物 1

HCID 57750416Tert-butyl 2-acetamido-1-(4-chlorophenyl)ethylcarbamate収率 62.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of tert-butyl 2-amino-1-(4-chlorophenyl)ethylcarbamate (Intermediate 73) (0.208 g, 0.77 mmol) and N-ethyldiisopropylamine (0.266 mL, 1.54 mmol) in THF (5 mL) was treated with acetic anhydride (0.102 mL, 1.08 mmol). The resulting solution was stirred at ambient temperature for 2 hours. The mixture was partitioned between DCM and sodium bicarbonate solution. The organic layer was concentrated and the residue was purified by flash column chromatography on silica using gradient elution (10% ethyl acetate/DCM to 40% ethyl acetate/DCM). The desired product, tert-butyl 2-acetamido-1-(4-chlorophenyl)ethylcarbamate (0.151 g, 62.7%), was thus isolated as a colourless solid.

後処理

  1. customThe mixture was partitioned between DCM and sodium bicarbonate solution
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by flash column chromatography on silica using gradient elution (10% ethyl acetate/DCM to 40% ethyl acetate/DCM)

出典と根拠

ORDレコード
ord-68bdbc6c635d484f94df78bc9ed2ddb4
出典データセット
uspto-grants-2012_01
特許番号
US08101623B2

反応ノート

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