Methanol → 5-Acetoxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

HRID 569080노트

반응식

HRID 569080 반응식
C(OC(N=NC(OCC)=O)=O)C.[CH2:13]([O:15][C:16]([CH:18]1[CH:30]([CH2:31][O:32][CH3:33])[C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][C:27]=3[CH2:34][O:35][C:36](=[O:38])[CH3:37])[NH:22][C:21]=2[CH:20](C(O)=O)[NH:19]1)=[O:17])[CH3:14].ClCCl.CO>O=O>[CH2:13]([O:15][C:16]([C:18]1[N:19]=[CH:20][C:21]2[NH:22][C:23]3[C:28]([C:29]=2[C:30]=1[CH2:31][O:32][CH3:33])=[C:27]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[CH:26]=[CH:25][CH:24]=3)=[O:17])[CH3:14]

참가 물질

6

반응물 4

HCID 887MethanolHCID 6344DichloromethaneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 201323905-Acetoxymethyl-4-methoxymethyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid-3 ethyl ester

생성물 1

HCID 138503625-Acetoxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester수율 98.3%

시약·촉매·용매 1

HCID 977Oxygen용매

실험 절차

90% Azodicarboxylic acid diethyl ester (76 ml) without addition of heat with stirring is added drop by drop to a solution of 5-acetoxymethyl-4-methoxymethyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid-3-ethyl ester (75 g) in oxygen-free dichloromethane (0.6 l) under argon protection. The temperature rises about 10° C. Reflux is performed for about 9 hours, then the mixture is left at room temperature for 60 hours. The precipitate is suctioned off, further end product can be obtained from the evaporated mother liquor after chromatography on silica gel with a mixture of dichloromethane (95%) with methanol (5%). Altogether 65 g of the title compound in the form of colorless crystals with a melting point of 129°-133° C. is obtained.

후처리

  1. temperatureof heat
  2. customrises about 10° C
  3. temperatureReflux
  4. waitthe mixture is left at room temperature for 60 hours
  5. customfurther end product can be obtained from the evaporated mother liquor after chromatography on silica gel

출처 및 근거

ORD 기록
ord-c9c8f4abbac041a0bf1cdb8b0633c1d3
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04731365

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