Methanol → (((4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl)amino)(4-hydroxyphenyl)acetic acid

HRID 67699

반응식

HRID 67699 반응식
OC1C=CC([NH:8][CH2:9][C:10]([OH:12])=[O:11])=CC=1.C[Si]([CH:17]([Si](C)(C)C)[C:18](N)=O)(C)C.[CH2:25]1[O:28][CH:26]1[CH3:27].[CH2:29]([N:31]1[CH2:36][CH2:35][N:34]([C:37](Cl)=[O:38])[C:33](=[O:40])[C:32]1=[O:41])[CH3:30].[CH3:42]O>C1COCC1>[CH2:29]([N:31]1[CH2:36][CH2:35][N:34]([C:37]([NH:8][CH:9]([C:18]2[CH:17]=[CH:27][C:26]([OH:28])=[CH:25][CH:42]=2)[C:10]([OH:12])=[O:11])=[O:38])[C:33](=[O:40])[C:32]1=[O:41])[CH3:30]

참가 물질

7

반응물 5

HCID 887MethanolHCID 6378Propylene OxideHCID 67149N-(4-Hydroxyphenyl)glycineHCID 1088134-Ethyl-2,3-dioxopiperazinecarbonyl chlorideHCID 11708267Bistrimethylsilylacetamid

생성물 1

HCID 3018895(((4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl)amino)(4-hydroxyphenyl)acetic acid수율 40%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a suspension of 8.3 g. (50 mmole) of 4-hydroxyphenylglycine in 75 ml. of tetrahydrofuran were added 25 ml. of bis-trimethylsilylacetamide and the suspension was stirred at room temperature for 15 minutes and then at 75° C. for 2.5 hours to form a solution. The solution was cooled to 0° C. and 25 ml. of propylene oxide were added. Next a solution of 11 g. of 4-ethylpiperazin-2,3-dione-1-ylcarbonyl chloride in 100 ml. of THF was added and the reaction mixture was stirred for 1 hour at 0° C. and at room temperature for 4 hours. Methyl alcohol, 40 ml., were added to the reaction mixture and after stirring for 15 minutes the mixture was evaporated to dryness. The gummy residue was dissolved in a mixture of ethyl acetate-aqueous sodium bicarbonate and the aqueous layer was separated, washed with ethyl acetate, filtered, and cooled to 0° C. The cold solution was layered with 200 ml. of fresh ethyl acetate and the pH adjusted to pH 1.9 with concentrated hydrochloric acid. The organic phase was separated, combined with an ethyl acetate wash of the acidified aqueous phase and dried over sodium sulfate. Evaporation of the dried organic phase gave 6.7 g. (40% yield) of α-(4-ethylpiperazin-2,3-dione-1-ylcarbonylamino)-4-hydroxyphenylacetic acid.

후처리

  1. additionTo a suspension of 8.3 g
  2. customat 75° C. for 2.5 hours to form a solution
  3. addition, were added to the reaction mixture
  4. stirringafter stirring for 15 minutes the mixture
  5. customwas evaporated to dryness
  6. dissolutionThe gummy residue was dissolved in a mixture of ethyl acetate-aqueous sodium bicarbonate
  7. customthe aqueous layer was separated
  8. washwashed with ethyl acetate
  9. filtrationfiltered
  10. temperaturecooled to 0° C
  11. customThe organic phase was separated
  12. washwash of the acidified aqueous phase
  13. dry with materialdried over sodium sulfate
  14. customEvaporation of the dried organic phase
  15. customgave 6.7 g

출처 및 근거

ORD 기록
ord-742c8fd720994516bfdd1a5645a8e425
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04346076

연결된 노트

불러오는 중…