Diisopropylethylamine → HCID 57595487, 화합물

HRID 1785987노트

반응식

HRID 1785987 반응식
[C:1]([O:4][CH2:5][C:6]([N:8]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C@H:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C@@H:11]([CH3:19])[CH2:10]1)=[O:7])(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:37]([C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][C:48]([CH3:54])([CH3:53])[C:49]([O:51][CH3:52])=[O:50])=[CH:41][CH:40]=1)=[O:38]>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]([N:8]([C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)[C@H:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:37]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][C:48]([CH3:54])([CH3:53])[C:49]([O:51][CH3:52])=[O:50])=[CH:41][CH:40]=2)=[O:38])[C@@H:11]([CH3:19])[CH2:10]1)=[O:7])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 57421380HCID 57421380, 화합물HCID 68921124HCID 68921124, 화합물

생성물 1

HCID 57595487HCID 57595487, 화합물수율 40%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-{(4-chlorophenyl)[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}-2-oxoethyl acetate (170 mg, 0.45 mmol, 1 equ.) in methylene chloride (2.0 mL) at room temperature was added diisopropylethylamine (127 uL, 0.73 mmol, 1.60 equ.) followed by methyl 5-[4-(chlorocarbonyl)phenyl]-2,2-dimethylpentanoate (196 mg, 0.73 mmol, 1.60 equ.). The reaction was stirred over night at room temperature. The mixture was concentrated, then poured into water and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulfate, filtered dried and concentrated. The crude residue was purified by silica gel chromatography (ethyl acetate/hexane 25/75 to 1:1 gradient) to afford the pure methyl 5-(4-{[(2S,4R)-4-[[(acetyloxy)acetyl](4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoate (110 mg, 40%).

후처리

  1. concentrationThe mixture was concentrated
  2. additionpoured into water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customdried
  8. concentrationconcentrated
  9. customThe crude residue was purified by silica gel chromatography (ethyl acetate/hexane 25/75 to 1:1 gradient)

출처 및 근거

ORD 기록
ord-d66277e98d1f4a59a5cad9023b6c3b9e
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504508B2

반응 노트

불러오는 중…