Hydrochloric Acid → HCID 131727621, 화합물

HRID 731520노트

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HRID 731520 반응식
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][C:4](=[O:6])[NH2:5].C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C.[NH2:36][C@H:37]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[CH:41][CH:40]=1.Cl.CN1CCOCC1>ClCCl.CN(C=O)C>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([NH:36][C@H:37]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([O:45][C:46]([CH3:49])([CH3:47])[CH3:48])=[CH:43][CH:44]=1)=[O:9])[CH2:3][C:4](=[O:6])[NH2:5]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 12734DiisopropylcarbodiimideHCID 757711-Hydroxybenzotriazole2회HCID 82035N2-((tert-Butoxy)carbonyl)-L-asparagineHCID 7350495Tert-butyl (2S)-2-amino-3-[4-(tert-butoxy)phenyl]propanoate

생성물 1

HCID 131727621HCID 131727621, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

Boc-Asn-OH (3.5 g 15 mmol) is dissolved in dichloromethane (100 ml amylene stabilised free of alcohol) and HOBt (2.24 g dry 16.5 mmol) is added. The mixture is cooled in an ice/water bath and DIC (2.45 ml 16 mmol) is added. The mixture will be allowed to react for 20 min. The HOBt on the bottom will react and a precipitate of DIU (on top) will form. H-Tyr(tBu)-OtBu×HCl (5.1 g 15.4 mmol) is dissolved in DMF (30 ml dry). The dichloromethane mixture containing the activated ester is filtered from the DIU directly into the DMF solution. The combined mixture is cooled in ice/water and NMM (1.75 ml 15.8 mmol) is added. The mixture is allowed to react over night. The solvents will be removed in vacuo. Ethyl acetate 200 ml is added and a precipitate is removed and the solution is washed with citric acid (2×50 ml 10%), sodium hydrogen carbonate (2×50 ml saturated) and brine (2×50 ml). The solution is dried with magnesium sulfate and the solvent removed in vacuo ending at 0.2 mBar for 30 min. The raw product will be suspended in pentane (40 ml) and filtered from a precipitate of DIU. The pentane will be removed in vacuo yielding the title compound.

후처리

  1. temperatureThe mixture is cooled in an ice/water bath
  2. customto react for 20 min
  3. customa precipitate of DIU (on top) will form
  4. filtrationis filtered from the DIU directly into the DMF solution
  5. temperatureThe combined mixture is cooled in ice/water
  6. customto react over night
  7. customThe solvents will be removed in vacuo
  8. additionEthyl acetate 200 ml is added
  9. customa precipitate is removed
  10. washthe solution is washed with citric acid (2×50 ml 10%), sodium hydrogen carbonate (2×50 ml saturated) and brine (2×50 ml)
  11. dry with materialThe solution is dried with magnesium sulfate
  12. customthe solvent removed in vacuo
  13. filtrationfiltered from a precipitate of DIU
  14. customThe pentane will be removed in vacuo

출처 및 근거

ORD 기록
ord-149181ff9f0b411ab915340f7bedcfde
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585839B2

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