Hydrochloric Acid → HCID 178484085, compound

HRID 1063634Notes

Reaction equation

HRID 1063634 reaction equation
[CH3:1][NH:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1.Cl.C[Si](C)(C)N[Si](C)(C)C.[CH:23]1[C:28]([O:29][C:30](Cl)=[O:31])=[CH:27][CH:26]=[C:25]([Cl:33])[CH:24]=1.[OH-].[Na+].Cl>O>[Cl:33][C:25]1[CH:26]=[CH:27][C:28]([O:29][C:30]([N:2]([CH2:3][C@H:4]2[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]2)[CH3:1])=[O:31])=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 13838HexamethyldisilazaneHCID 14798Sodium HydroxideHCID 1390594-Chlorophenyl chloroformateHCID 178484084HCID 178484084, compound

Product 1

HCID 178484085HCID 178484085, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

0.60 g (2.89 mmol) of trans-4-methylaminomethyl-cyclohexanecarboxylic acid·HCl were mixed with 7.57 mL (36.28 mmol, 12.5 eq) of hexamethyldisilazane and heated under reflux to 140° C. for 2.5 h. The solution was evaporated, dissolved in 6 mL of THF and treated with 0.45 mL (3.18 mmol, 1.1 eq) of 4-chlorophenylchloroformate at 0° C. and stirred at RT overnight. Then 3 mL of water were added at RT followed by 10 mL of 1M NaOH. After stirring for 1 h at RT 15 mL of 1M HCl were added. The solution was then partitioned between EtOAc (×3)/H2O, dried over Na2SO4 and evaporated to yield 0.92 g (98%) of trans-4-{[(4-chloro-phenoxycarbonyl)-methyl-amino]-methyl}-cyclohexane carboxylic acid, MS: 324 (M−H−, 1Cl).

Workup

  1. temperatureheated
  2. customThe solution was evaporated
  3. dissolutiondissolved in 6 mL of THF
  4. additionwere added
  5. customThe solution was then partitioned between EtOAc (×3)/H2O
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-ff19d28bebbe401b9d068728a0a01880
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

Loading…