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

HRID 845234ノート

反応式

HRID 845234 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 977Oxygen溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0fa1f16296384b7e92fb594fdf6ec3d1
出典データセット
uspto-grants-1988_07
特許番号
US04757070

反応ノート

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