Tert-Butylamine → N-(carbobenzyloxy)-3-(2-thienyl)-L-alanine-tert butylamide

HRID 400196

반응식

HRID 400196 반응식
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:19]([OH:21])=O)[CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(N[C@H](C(O)=O)CC1SC=CC=1)=O)C1C=CC=CC=1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.[C:58]([NH2:62])([CH3:61])([CH3:60])[CH3:59]>C1COCC1>[C:58]([NH:62][C:19](=[O:21])[C@H:12]([CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])([CH3:61])([CH3:60])[CH3:59]

참가 물질

7

반응물 5

HCID 6385Tert-ButylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 128068302-{[(Benzyloxy)carbonyl]amino}-3-(thiophen-2-yl)propanoic acidHCID 53725744(2S)-2-Amino-3-(thien-2-yl)propanoic acid, N-CBZ protected

생성물 1

HCID 22858355N-(carbobenzyloxy)-3-(2-thienyl)-L-alanine-tert butylamide수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Into a 500 ml flask was placed 8.06 g of the subtitled compound of Example A, N-(Benzyloxycarbonyl)-3-(2-thienyl)-L-alanine, in 130 ml of THF. The compound was cooled to 0° C. N-Methylmorpholine (4.23 ml) was added, followed by isobutylchloroformate (4.04 ml) over two minutes. The mixture was stirred for 15-20 minutes, and 3.74 ml of t-butylamine was added. The bath was removed, and the mixture was stirred at room temperature for two hours. The mixture was concentrated on rotovap, and the residue was taken up in ethyl acetate. The residue was washed successively with H2O, HCl, and saturated NaHCO3 solution. The organics were separated and dried with Na2SO4, filtered, and concentrated to an oil. The oil was dissolved in 100 ml hot hexane and cooled in a refrigerator overnight to give a solid. The hexane was decanted, followed by drying to yield a solid of 9.25 g N-(carbobenzyloxy)-3-(2-thienyl)-L-alanine-tert-butylamide (97% yield).

후처리

  1. customInto a 500 ml flask was placed
  2. customThe bath was removed
  3. stirringthe mixture was stirred at room temperature for two hours
  4. concentrationThe mixture was concentrated on rotovap
  5. washThe residue was washed successively with H2O, HCl, and saturated NaHCO3 solution
  6. customThe organics were separated
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to an oil
  10. dissolutionThe oil was dissolved in 100 ml hot hexane
  11. temperaturecooled in a refrigerator overnight
  12. customto give a solid
  13. customThe hexane was decanted
  14. customby drying

출처 및 근거

ORD 기록
ord-032f48892ca349af8be7f1922f178e36
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05827859

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