4-Ethylphenyl isocyanate → 4-(2-Chlorobenzylamino)-3,3-dimethyl-4-oxobutyl 4-ethylphenylcarbamate

HRID 655956

反応式

HRID 655956 の反応式
[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][NH:5][C:6](=[O:13])[C:7]([CH3:12])([CH3:11])[CH2:8][CH2:9][OH:10].[CH2:18]([C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1)[CH3:19]>C1COCC1.CN(C1C=CN=CC=1)C>[CH2:18]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:28])[O:10][CH2:9][CH2:8][C:7]([CH3:12])([CH3:11])[C:6]([NH:5][CH2:4][C:3]2[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=2[Cl:1])=[O:13])=[CH:22][CH:21]=1)[CH3:19]

参加物

5

反応物 2

HCID 900074-Ethylphenyl isocyanateHCID 59778491N-(2-chlorobenzyl)-4-hydroxy-2,2-dimethylbutanamide

生成物 1

HCID 250264164-(2-Chlorobenzylamino)-3,3-dimethyl-4-oxobutyl 4-ethylphenylcarbamate収率 25%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-(2-chlorobenzyl)-4-hydroxy-2,2-dimethylbutanamide (400 mg, 1.6 mmol) in THF (25 mL) were added 4-ethylphenylisocyanate (276 μL, 1.92 mmol, 1.2 equiv.) and DMAP (293 mg, 2.4 mmol, 1.5 equiv.). The reaction mixture was stirred overnight. The reaction mixture was concentrated. The resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O, and further purified by flash column chromatography using a mixture of hexanes and EtOAc to give 4-(2-chlorobenzylamino)-3,3-dimethyl-4-oxobutyl 4-ethylphenylcarbamate (160 mg, 25%). LRMS (M+H+) m/z 403.1.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customThe resulting residue was purified on RP-HPLC
  3. additiona mixture of acetonitrile and H2O
  4. customfurther purified by flash column chromatography
  5. additiona mixture of hexanes and EtOAc

出典と根拠

ORDレコード
ord-5a3700b4a789410c9586979b71c72201
出典データセット
uspto-grants-2011_12
特許番号
US08071625B2

関連ノート

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