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

HRID 655956

반응식

HRID 655956 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5a3700b4a789410c9586979b71c72201
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071625B2

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