Potassium Carbonate → 5-Acetoxymethyl-4-methoxymethyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid-3 ethyl ester

HRID 845233ノート

反応式

HRID 845233 の反応式
[CH2:1]([O:3][C:4](=[O:25])[CH:5]([NH2:24])[CH:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:19][O:20][C:21](=[O:23])[CH3:22])[NH:12][CH:11]=1)[CH2:7][O:8][CH3:9])[CH3:2].O.[C:27]([OH:31])(=[O:30])[CH:28]=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH2:1]([O:3][C:4]([CH:5]1[CH:6]([CH2:7][O:8][CH3:9])[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[CH2:19][O:20][C:21](=[O:23])[CH3:22])[NH:12][C:11]=2[CH:28]([C:27]([OH:31])=[O:30])[NH:24]1)=[O:25])[CH3:2]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 15620607Glyoxylic acid, monohydrateHCID 539291523-(4-Acetoxymethylindol-3-yl)-2-amino-4-methoxy-butyric acid ethyl ester

生成物 1

HCID 201323905-Acetoxymethyl-4-methoxymethyl-1,2,3,4-tetrahydro-beta-carboline-1,3-dicarboxylic acid-3 ethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A solution of 3-(4-acetoxymethylindol-3-yl)-2-amino-4-methoxy-butyric acid ethyl ester (8.7 g) in ethyl acetate (40 ml) is slowly added drop by drop to a solution of glyoxylic acid monohydrate (2.4 g) in water (30 ml), cooled to 0° C., under argon protection and with stirring. The pH of the solution is adjusted to 4 by addition of potassium carbonate (about 1 g). Then the mixture is stirred for 2 hours, whereby it is allowed to warm to room temperature. Ethyl acetate and water phases are separated, the water phase is shaken out three times with ethyl acetate. The combined ethyl acetate extracts, for their part, are washed once with water, dried with sodium sulfate and evaporated. 9 g of the title compound remains.

後処理

  1. stirringThen the mixture is stirred for 2 hours
  2. temperatureto warm to room temperature
  3. customEthyl acetate and water phases are separated
  4. stirringthe water phase is shaken out three times with ethyl acetate
  5. washare washed once with water
  6. dry with materialdried with sodium sulfate
  7. customevaporated

出典と根拠

ORDレコード
ord-fb09866dd06c442a8b4d97e101b92b5f
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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