Tyramine → HCID 21091234, 화합물

HRID 351133

반응식

HRID 351133 반응식
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][Cl:8].C([N:11]([CH2:14]C)[CH2:12][CH3:13])C.ClC(OCC)=[O:18].ClC(OC)=S.ClCCNCCCl.NCCC1C=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1>ClCCl.C(OCC)(=O)C>[Cl:2][CH2:3][CH2:4][N:5]([C:14]([NH:11][C:12]1[CH:13]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)=[O:18])[CH2:6][CH2:7][Cl:8]

참가 물질

9

반응물 6

HCID 5610TyramineHCID 8471TriethylamineHCID 9533Bis(2-chloroethyl)amineHCID 10928Ethyl chloroformateHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 554404Methyl chloromethanethioate

생성물 1

HCID 21091234HCID 21091234, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

One pot method. bis-(2-Chloroethyl)amine hydrochloride 26 (200 mg, 1.1 mmol) was dissolved in dichloromethane (15 mL) and triethylamine (0.45 mL, 3.3 mmol) was added. The mixture was stirred for 5 minutes at ambient temperature and ethyl chloroformate or methyl chlorothioformate (1.32 mmol) was added. The mixture was stirred until no bis-(2-chloroethyl)amine remained by TLC (ethyl acetate). Tyramine (300 mg, 2.2 mmol) was added and the mixture was heated under reflux for 4 hours. the mixture was allowed to cool, purified by dry flash column chromatography (silica gel, dichloromethane 200 cm3) and concentrated in vacuo to yield prodrug 28 as an orange/brown oil (234 mg, 67% for methyl chlorothioformate and 229 mg, 64% for ethyl chloroformate).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. custompurified
  5. dry with materialby dry flash column chromatography (silica gel, dichloromethane 200 cm3)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6f87aab0f5034d669aca154b543b3923
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183319B2

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