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Hydrochloric Acid → 3-[3-[[(1R,2R)-3-hydroxy-2-methyl-1-phenylpropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl ester

HRID 1697310
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HRID 1697310 반응식
CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][C@H:8]([CH3:23])[C@@H:9]([NH:16][S@@](C(C)(C)C)=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)C.Cl.Br[C:38]1[C:39](=[O:56])[N:40]([C:45]2[CH:46]=[C:47]([CH:52]=[CH:53][C:54]=2[CH3:55])[C:48]([O:50][CH3:51])=[O:49])[CH:41]=[C:42](Br)[N:43]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1.C(OCC)(=O)C.O1CCCC1.CO>[OH:6][CH2:7][C@H:8]([CH3:23])[C@@H:9]([NH:16][C:38]1[C:39](=[O:56])[N:40]([C:45]2[CH:46]=[C:47]([CH:52]=[CH:53][C:54]=2[CH3:55])[C:48]([O:50][CH3:51])=[O:49])[CH:41]=[CH:42][N:43]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1
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참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 66688740methyl 3-(3,5-dibromo-2-oxopyrazin-1(2H)-yl)-4-methylbenzoateHCID 66690258(R)-N-[(1R,2R)-3-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-methyl-1-phenylpropyl]-2-methyl-2-propanesulfinamide

생성물 1

HCID 866632413-[3-[[(1R,2R)-3-hydroxy-2-methyl-1-phenylpropyl]amino]-2-oxo-1(2H)-pyrazinyl]-4-methyl-benzoic acid, methyl ester
수율 98.7%

시약·촉매·용매 4

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
50 °C

실험 절차

A mixture of (R)—N-[(1R,2R)-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-methyl-1-phenylpropyl]-2-methyl-2-propanesulfinamide (Example 136b, 5.2 g), methanol (25 mL) and a solution of hydrogen chloride in 1,4-dioxane (4M, 25 mL) was stirred at 50° C. for 7 h and left at room temperature for 70 h. The mixture was concentrated in vacuo and the residue was washed with ether to give the crude amine hydrochloride (2.0 g). 3-(3,5-Dibromo-2-oxo-2H-pyrazin-1-yl)-4-methyl-benzoic acid, methyl ester (Example 1b, 3.5 g) was added followed by N,N-diisopropylethylamine (4 mL) and tetrahydrofuran (50 mL). The mixture was stirred at 50° C. for 24 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (200 mL) and washed with sat. aqueous NaHCO3. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. Ethanol (50 mL) was added under nitrogen atmosphere followed by wet palladium on carbon (10%, 227 mg), ammonium formate (3 g) and N,N-diisopropylethylamine (2 mL). The mixture was stirred at 70° C. for 2 h, cooled to room temperature, filtered through a pad of Celite and concentrated in vacuo. The residue was diluted with ethyl acetate (200 mL) and washed with water. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to give the subtitle compound (3.5 g).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. washthe residue was washed with ether
  3. customto give the crude amine hydrochloride (2.0 g)
  4. temperatureAfter cooling to room temperature
  5. washwashed with sat. aqueous NaHCO3
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionEthanol (50 mL) was added under nitrogen atmosphere
  10. stirringThe mixture was stirred at 70° C. for 2 h
  11. temperaturecooled to room temperature
  12. filtrationfiltered through a pad of Celite
  13. concentrationconcentrated in vacuo
  14. additionThe residue was diluted with ethyl acetate (200 mL)
  15. washwashed with water
  16. dry with materialThe organic phase was dried (Na2SO4)
  17. filtrationfiltered
  18. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a44ffc64bf63407ab342fef1106b4657
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163905B2

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