Malic Acid → O-(4-hexadecylamino-2-thiophenecarbonyl)malic acid

HRID 850986노트

반응식

HRID 850986 반응식
C([N:11]([C:28]1[CH:29]=[C:30]([C:33](Cl)=[O:34])[S:31][CH:32]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(OCC1C=CC=CC=1)=O.C(N(CC)CC)C.[C:43]([OH:51])(=[O:50])[CH:44]([CH2:46][C:47]([OH:49])=[O:48])[OH:45].[H][H]>O1CCCC1.[Pd].CCOCC>[CH2:12]([NH:11][C:28]1[CH:29]=[C:30]([C:33]([O:50][C:43](=[O:51])[CH:44]([CH2:46][C:47]([OH:49])=[O:48])[OH:45])=[O:34])[S:31][CH:32]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

참가 물질

8

반응물 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 205036214-[N-(carbobenzyloxy)-N-hexadecylamino]-2-thiophenecarbonyl chlorideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 86738856O-(4-hexadecylamino-2-thiophenecarbonyl)malic acid

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A warm solution of 4-[N-(carbobenzyloxy)-N-(hexadecyl)amino]-2-thiophenecarbonyl chloride and 1.3 g. of triethylamine in 100 ml. ether is treated with 2 g. malic acid. An immediate precipitate forms, but the mixture is refluxed for one hour and filtered while hot. The solid is washed several times with hot ether; then the ether is evaporated to yield a white solid. The product is dissolved in tetrahydrofuran (100 ml.) and hydrogenated over 600 mg. 10% palladium-on-carbon at 50 psi until hydrogen uptake stops. The catalyst is filtered, and the solution is evaporated. The residue is crystallized from acetic acid to yield the product as a white solid.

후처리

  1. temperatureAn immediate precipitate forms, but the mixture is refluxed for one hour
  2. filtrationfiltered while hot
  3. washThe solid is washed several times with hot ether
  4. customthen the ether is evaporated
  5. customto yield a white solid
  6. filtrationThe catalyst is filtered
  7. customthe solution is evaporated
  8. customThe residue is crystallized from acetic acid

출처 및 근거

ORD 기록
ord-dd278f15741c4545b496cd60e1156566
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04382143

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