Hydrochloric Acid → HCID 59432811、化合物

HRID 507318ノート

反応式

HRID 507318 の反応式
[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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 14163092HCID 14163092、化合物

生成物 1

HCID 59432811HCID 59432811、化合物収率 50.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e5e5d0edf8bb4ba8b511ad18aaee22cc
出典データセット
uspto-grants-2010_08
特許番号
US07786122B2

反応ノート

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