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Hydrochloric Acid → (S)-2-Amino-4-methyl-pentanoic acid [4,4-bis-(4-fluoro-phenyl)-butyl]-amide monohydrochloride

HRID 990331
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HRID 990331 반응식
C(OC(=O)[NH:7][C@H:8]([C:13](=[O:33])[NH:14][CH2:15][CH2:16][CH2:17][CH:18]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.FC(F)(F)C(O)=O.[ClH:42].C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)C>[ClH:42].[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH:18]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH2:17][CH2:16][CH2:15][NH:14][C:13](=[O:33])[C@@H:8]([NH2:7])[CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:24][CH:23]=1
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참가 물질

7

반응물 4

HCID 313Hydrochloric Acid2회HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 12017807(S)-{1-[4,4-Bis-(4-fluoro-phenyl)-butylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester

생성물 1

HCID 86758543(S)-2-Amino-4-methyl-pentanoic acid [4,4-bis-(4-fluoro-phenyl)-butyl]-amide monohydrochloride

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (S)-{1-[4,4-bis-(4-fluoro-phenyl)-butylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester (1.4 g, 3.8 mmol, Example 6) in CH2Cl2 (15 mL) was added trifluoroacetic acid (5 mL) at ambient temperature under nitrogen atmosphere. The resulting reaction mixture was stirred for 25 minutes, then concentrated in vacuo. The viscous oil obtained was dissolved in 60 mL of CH2Cl2 and successively washed with saturated aqueous NaHCO3 solution (2×60 mL), brine (2×60 mL), and was dried over Na2SO4. The CH2Cl2 solution of free amine was concentrated in vacuo to afford the crude product as a viscous oil which was then dissolved in 10 mL of ethyl ether. To this solution was added saturated HCl solution in ethyl ether until no more white precipitate formed. Filtration and drying overnight under vacuum afforded 1.2 g (99.6%) of crude product. A portion of the crude product, a HCl salt, was converted back to the free amine by treatment with saturated aqueous NaHCO3 solution; the crude free amine was further purified by flash chromatography (straight EtOAc, then 10% MeOH in HCCl3) and converted into HCl salt as described above. Pure titled compound was obtained as a white foam (0.3 g); mp 65-80° C. APCI-MS m/z 375.3 (MH+).

후처리

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. customThe viscous oil obtained
  4. washsuccessively washed with saturated aqueous NaHCO3 solution (2×60 mL), brine (2×60 mL)
  5. dry with materialwas dried over Na2SO4
  6. concentrationThe CH2Cl2 solution of free amine was concentrated in vacuo
  7. customto afford the crude product as a viscous oil which
  8. customformed
  9. filtrationFiltration
  10. customdrying overnight under vacuum
  11. customafforded 1.2 g (99.6%) of crude product
  12. customthe crude free amine was further purified by flash chromatography (straight EtOAc

출처 및 근거

ORD 기록
ord-85c5b22023274fc09529c0c7366a11e1
출처 데이터셋
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06458781B1

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