Benzyl chloroformate → 4-(((Benzyloxy)(hydroxy)methylidene)amino)cyclohexane-1-carboxylic acid

HRID 1432413Notes

Reaction equation

HRID 1432413 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]1.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH2:5]([O:4][C:2]([NH:12][CH:13]1[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 1715604-Aminocyclohexanecarboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 2852474-(((Benzyloxy)(hydroxy)methylidene)amino)cyclohexane-1-carboxylic acidYield 59.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl chloroformate (2.2 mL, 15.4 mmol) was added to a solution of 4-amino-cyclohexanecarboxylic acid (2 g, 14.0 mmol) in a mixture of 1,4-dioxane (5 mL) and saturated sodium bicarbonate aqueous solution (5 mL). The mixture was stirred at 0° C. for 3 hours. Dioxane was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The ethyl acetate solution was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 2.3 g (59%) of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid as yellow oil. MS (ESP−) m/z 276.39 (M−1). 1H NMR (300 MHz, CDCl3) δ 7.34 (m, 5H), 5.09 (s, 2H), 2.24 (m, 1H), 2.04 (m, 2H), 1.83 (m, 2H), 1.44 (m, 3H), 0.97 (m, 2H).

Workup

  1. customDioxane was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe ethyl acetate solution was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6c69283da5d7425f8e8e14bb48941e17
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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