Hydrochloric Acid → 2-(((Benzyloxy)carbonyl)amino)cyclohexane-1-carboxylic acid

HRID 1593990Notes

Reaction equation

HRID 1593990 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=[O:19])C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl.C(OCC)(=[O:27])C>O1CCCC1.O>[CH2:1]([O:8][C:9]([NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17]([OH:19])=[O:27])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 20732580(2-Acetyl-cyclohexyl)-carbamic acid benzyl ester

Product 1

HCID 125126072-(((Benzyloxy)carbonyl)amino)cyclohexane-1-carboxylic acidYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester of step 1 (26.45 g, 86.62 mmol) was dissolved in 250 mL of tetrahydrofuran and treated with a solution of lithium hydroxide monohydrate (10.65 g, 256 mmol) in 250 mL of water and stirred at ambient temperature for 24 h. The reaction mixture was cooled to 0° C. and neutralized with 300 mL of a 1N HCl solution. Ethyl acetate (400 mL) was added and the organic layer was separated, dried over sodium sulfate, filtered and concentrated to give a crude solid. The product was purified by recrystallizing from ethyl acetate/hexanes to give 19.60 g of a white solid. Yield: 82%, MS: 278 (M+H+), mp=120.1-123.1° C.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude solid
  6. customThe product was purified
  7. customby recrystallizing from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f05fc82289ed47e7b2ac60f52afa8234
Source dataset
uspto-grants-2007_11
Patent number
US07300934B2

Reaction notes

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