Hydrochloric Acid → HCID 59432811, 화합물

HRID 507318노트

반응식

HRID 507318 반응식
[NH2:1][CH:2]([CH2:8][C:9]([CH3:11])=[CH2:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.CCN(CC)CC.Cl>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][CH:2]([CH2:8][C:9]([CH3:11])=[CH2:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:21])=[O:20])=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 14163092HCID 14163092, 화합물

생성물 1

HCID 59432811HCID 59432811, 화합물수율 50.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of ethyl 2-amino-4-methyl-4-pentenoate (2.84 g, 18.1 mmol, prepared as in Reaction Scheme 19 from (benzhydrylideneamino)acetic acid ethyl ester and 1-bromo-2-methyl-2-propene) in CH2Cl2 (250 mL) was reacted with 4-chlorobenzenesulfonyl chloride (4.20 g, 19.9 mmol) and Et3N (3.78 mL, 27.2 mmol). After 4 h, the resulting mixture was poured into 1 N aqueous HCl (500 mL) and extracted with EtOAc (3×150 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo. The crude concentrate was purified using silica gel column chromatography (10:1 to 5:1 gradient, hexanes/EtOAc) to afford 3.04 g (25% yield over 3 steps) of ethyl 2-(4-chlorobenzenesulfonylamino)-4-methyl-4-pentenoate: LCMS (M+Na)+ 354.2; 1H NMR (400 MHz, CDCl3) 7.77 (d, 2H, J=9.1), 7.46 (d, 2H, J=8.8), 5.07 (d, 1H, J=9.0), 4.84 (s, 1H), 4.73 (s, 1H), 4.05 (m, 1H), 3.95 (q, 2H, J=7.1), 2.40 (m, 2H), 1.66 (s, 3H), 1.13 (t, 3H, J=7.1).

후처리

  1. extractionextracted with EtOAc (3×150 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationThe crude concentrate
  7. customwas purified

출처 및 근거

ORD 기록
ord-e5e5d0edf8bb4ba8b511ad18aaee22cc
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786122B2

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