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

HRID 845233노트

반응식

HRID 845233 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fb09866dd06c442a8b4d97e101b92b5f
출처 데이터셋
uspto-grants-1988_07
특허 번호
US04757070

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