Sodium Hydroxide → HCID 178485999, Verbindung

HRID 1063631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1063631
[CH2:1]([O:8][C:9](=[O:19])[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:24][C:25](=[O:28])[CH2:26]Br)(C)(C)C.[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][C:9]([N:10]([CH3:11])[C@H:12]1[CH2:17][CH2:16][C@H:15]([O:18][CH2:26][C:25]([OH:28])=[O:24])[CH2:14][CH2:13]1)=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetate2×HCID 178485998HCID 178485998, Verbindung

Produkt 1

HCID 178485999HCID 178485999, VerbindungAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysator2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of 15.0 g (57 mmol) of trans-(4-hydroxy-cyclohexyl)-methyl-carbamic acid benzyl ester in 230 mL of toluene were added 16.8 mL (114 mmol, 2 eq) of bromo-acetic acid tert-butyl ester and 1.93 g (5.7 mmol, 0.1 eq) of tetra-n-butylammonium hydrogensulfate and 400 mL of 50% aqueous NaOH. The mixture was stirred at RT for 4 h, additional 1.93 g (5.7 mmol, 0.1 eq) of tetra-n-butylammonium hydrogensulfate and 4.2 mL of bromo-acetic acid tert-butyl ester were added and stirring was continued over night. The solution was concentrated and acidified by addition of 400 mL of 37% HCl. The solution was extracted with EtOAc, the organic phase was washed with brine and dried over Na2SO4. The solvent was removed to yield 18.2 g (quantitative) of trans-[4-(benzyloxycarbonyl-methyl-amino)-cyclohexyloxy]-acetic acid as white solid, MS: 320 (M−H)−.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued over night
  3. concentrationThe solution was concentrated
  4. additionacidified by addition of 400 mL of 37% HCl
  5. extractionThe solution was extracted with EtOAc
  6. washthe organic phase was washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-9aa74da2d9b54171a191403721f8b792
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06965048B2

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