Salicylic Acid → Tert-butyl 2-(2-(2-(2-hydroxybenzamido)ethyl)disulfanyl)ethylcarbamate

HRID 1525992노트

반응식

HRID 1525992 반응식
[NH2:1][CH2:2][CH2:3][S:4][S:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[C:16](O)(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19].CCN=C=NCCCN(C)C>C(Cl)Cl>[OH:19][C:18]1[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=1[C:16]([NH:1][CH2:2][CH2:3][S:4][S:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:24]

참가 물질

5

반응물 3

HCID 338Salicylic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22245556tert-butyl N-(2-((2-aminoethyl)disulfanyl)ethyl)carbamate

생성물 1

HCID 86643520Tert-butyl 2-(2-(2-(2-hydroxybenzamido)ethyl)disulfanyl)ethylcarbamate수율 54.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

tert-Butyl 2-(2-(2-aminoethyl)disulfanyl)ethylcarbamate (500 mg, 1.98 mmol) was taken up in CH2Cl2 (20 mL) along with salicylic acid (273 mg, 1.98 mmol) and EDCI (693 mmol, 2.2 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with CH2Cl2, washed with saturated aqueous NaHCO3, brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by chromatography (40% EtOAc, 60% pentane) afforded tert-butyl 2-(2-(2-(2-hydroxybenzamido)ethyl)disulfanyl)ethylcarbamate (400 mg, 54%). Mass calculated for C16H24N2O4S2: 372.12; found: [M+H]+=373.

후처리

  1. customThe resulting reaction mixture
  2. washwashed with saturated aqueous NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography (40% EtOAc, 60% pentane)

출처 및 근거

ORD 기록
ord-b644ee3fa83a47868215074561f6fba4
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085527B2

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