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

HRID 1350266
ノート
印刷プレビュー

反応式

HRID 1350266 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

(R)-2-[2-(tert-Butoxy)-2-oxoethyl]-5-phenylpentanoic acid cyclohexylamine salt (Preparation 166, 6.8 g, 17 mmol) and ethyl acetate (100 ml) were added to an aqueous solution of citric acid (10%, 100 ml) 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 room temperature, 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 room temperature where it 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).

後処理

  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 room temperature where it
  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

出典と根拠

ORDレコード
ord-002858efe08e4728bd3df6ded7b03557
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07214694B2

反応ノート

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