Triethylamine → 3-(4-Chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester

HRID 852555노트

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HRID 852555 반응식
Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH2:13])[CH:6]=1.CCN(CC)CC.[Cl:22][CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl.CCOC(C)=O>[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH:13][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][Cl:22])[CH:6]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 693575963-Amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride

생성물 1

HCID 693577003-(4-Chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester수율 103.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a solution of 3-amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride (D62) (0.13 g, 0.556 mmol, 1 equiv) in dry CH2Cl2 (2 ml) at 0° C. was added NEt3 (193 ml, 1.39 mmol, 2.5 equiv) then 4-chlorobutyryl chloride (69 ml, 0.612 mmol, 1.1 equiv), dropwise, over 2 min. The resulting solution was stirred at 0° C. for 15 min then at room temperature for 30 min. The solution was then diluted with AcOEt, washed sequentially with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo to give 3-(4-chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester (D64) (173 mg, 103%) as pale yellow crystals. [M+H]+=302.0, RT=3.20 min

후처리

  1. waitat room temperature for 30 min
  2. washwashed sequentially with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6ed46d440efe4513ae9c5a11f1d3fda9
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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