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Citric Acid → (R)-2-(2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid cyclohexylamine salt

HRID 1281255
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HRID 1281255 반응식
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[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.C1(N)CCCCC1>CO>[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[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]([OH:18])=[O:17])([CH3:11])([CH3:9])[CH3:10]
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참가 물질

6

반응물 4

HCID 311Citric AcidHCID 7965CyclohexylamineHCID 8857Ethyl AcetateHCID 69431039(r)-2-[2-(Tert-butoxy)-2-oxoethyl]-5-phenylpentanoic acid cyclohexylamine salt

생성물 1

HCID 69430977(R)-2-(2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid cyclohexylamine salt수율 71%

시약·촉매·용매 1

HCID 887
Methanol
용매

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온도
22.5 °C

실험 절차

(R)-2-[2-(tert-Butoxy)-2-oxoethyl]-5-phenylpentanoic acid cyclohexylamine salt (691 g, 1.77 mol) and ethyl acetate (7.0 liters) were added to an aqueous solution of citric acid (10%, 6.3 liters) and the organic phase was separated, washed with water (7.0 liters) and concentrated in vacuo to a yellow oil. A solution of the oil and 5% rhodium on carbon (51.6 g) in methanol (7.0 liters) 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 cyclohexylamine (202 ml, 1.77 mol) and the methanol solution was stripped and replaced with methylethyl ketone by distillation at atmospheric pressure, to a volume of 5.5 liters. The mixture was allowed to cool to 20-25° C. where it was stirred for 48 hours and then filtered. The residue was washed with methylethyl ketone (2×500 ml) and then dried in vacuo at 45° C. for 4 hours to leave the title compound as a colourless solid (495 g, 71% yield, 99% pure by HPLC).

후처리

  1. customthe organic phase was separated
  2. washwashed with water (7.0 liters)
  3. concentrationconcentrated in vacuo to a yellow oil
  4. filtrationfiltered through celite
  5. distillationreplaced with methylethyl ketone by distillation at atmospheric pressure, to a volume of 5.5 liters
  6. temperatureto cool to 20-25° C. where it
  7. stirringwas stirred for 48 hours
  8. filtrationfiltered
  9. washThe residue was washed with methylethyl ketone (2×500 ml)
  10. customdried in vacuo at 45° C. for 4 hours

출처 및 근거

ORD 기록
ord-9c3d9303c6d34670be0fc68466c10e97
출처 데이터셋
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06452041B1

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