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Citric Acid → (r)-2-[2-(Tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid sodium salt

HRID 1281256
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HRID 1281256 반응식
C1(N)CCCCC1.[C:8]([O:12][C:13](=[O:28])[CH2:14][C@@H:15]([CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]([OH:18])=[O:17])([CH3:11])([CH3:10])[CH3:9].C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[OH-].[Na+:49]>O>[Na+:49].[C:8]([O:12][C:13](=[O:28])[CH2:14][C@@H:15]([CH2:19][CH2:20][CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[C:16]([O-:18])=[O:17])([CH3:11])([CH3:9])[CH3:10]
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참가 물질

6

반응물 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 69431039(r)-2-[2-(Tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid cyclohexylamine salt

생성물 1

HCID 60077622(r)-2-[2-(Tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid sodium salt수율 69.8%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
22.5 °C

실험 절차

(R)-2-[2-(tert-Butoxy)-2-oxoethyl]-5-phenylpentanoic acid cyclohexylamine salt (6.8 g, 17 mmol) and ethyl acetate (100 ml) were added to an aqueous solution of citric acid (10%, 100ml) and the organic phase was separated and washed with water (100 ml). Iso-propyl alcohol (20 ml) and 5% rhodium on alumina (51.6 g) were added and the mixture was stirred at 20-25° C., under hydrogen (10 atmospheres, 150 p.s.i.) for 48 hours and then filtered through celite. To the filtrate was added a solution of sodium hydroxide (0.67 g, 17 mmol) in water and the mixture was stripped and replaced with acetonitrile by distillation at atmospheric pressure to a volume of 30 ml. The mixture was allowed to cool to 20-25° C. and was stirred for 24 hours. The mixture was cooled to 0° C. and then filtered. The residue was washed with acetonitrile (2×10 ml) and then dried in vacuo at 45° C. for 2 hours to leave the title compound as a colourless solid (3.8 g, 69% yield, 95% pure by NMR).

후처리

  1. customthe organic phase was separated
  2. washwashed with water (100 ml)
  3. additionIso-propyl alcohol (20 ml) and 5% rhodium on alumina (51.6 g) were added
  4. filtrationfiltered through celite
  5. distillationreplaced with acetonitrile by distillation at atmospheric pressure to a volume of 30 ml
  6. temperatureto cool to 20-25° C.
  7. stirringwas stirred for 24 hours
  8. temperatureThe mixture was cooled to 0° C.
  9. filtrationfiltered
  10. washThe residue was washed with acetonitrile (2×10 ml)
  11. customdried in vacuo at 45° C. for 2 hours

출처 및 근거

ORD 기록
ord-614d0d053b044ffab965125c8bf2c31e
출처 데이터셋
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06452041B1

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