Hydrochloric Acid → HCID 178485999, compound

HRID 2118231Notes

Reaction equation

HRID 2118231 reaction equation
[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+].Cl>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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetate2×HCID 178485998HCID 178485998, compound

Product 1

HCID 178485999HCID 178485999, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst2×HCID 1140TolueneSolvent

Procedure

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-butyl-ammoniumhydrogensulfate and 4.2 mL of bromo-acetic acid tert-butyl ester were added, and stirring was continued over night. The solution was concentated and acidified by adding 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) trans-[4-(benzyloxycarbonyl-methyl-amino)-cyclohexyloxy]-acetic acid as white solid, MS: 320 (M−H)−.

Workup

  1. stirringstirring
  2. waitwas continued over night
  3. extractionThe solution was extracted with EtOAc
  4. washthe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-a1fe029bb9e44818b2bf519e300b46a7
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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