Sodium Hydroxide → HCID 178453624, compound

HRID 1720454Notes

Reaction equation

HRID 1720454 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1.[C:14]([O:18][C:19](=O)[O:20]C(C)(C)C)([CH3:17])([CH3:16])[CH3:15]>O1CCOCC1>[C:14]([O:18][C:19]([NH:3][CH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]([OH:13])=[O:12])[CH2:9][CH2:10]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 178511262HCID 178511262, compound

Product 1

HCID 178453624HCID 178453624, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

63.6 ml of an N aqueous NaOH solution and 1.28 g of MgO are introduced, at 0° C., into 50 ml of dioxane containing 5 g of trans-4-(aminomethyl)cyclohexylcarboxylic acid, followed, slowly, by 6.94 g of di(t-butyl)carbonate in solution in 20 ml of dioxane. After 20 hours at room temperature, the mixture is filtered, the solvent is removed and the residue is taken up in 100 ml of H2O and the aqueous phase is washed with (C2H5)2O before acidifying it up to pH 2 by addition of KHSO)4 ; it is then extracted in CH3COOC2H5 to yield 7.3 g of trans-N-(t-butoxycarbonyl)-4-(aminomethyl)cyclohexylcarboxylic acid which melts at 125° C.

Workup

  1. filtrationthe mixture is filtered
  2. customthe solvent is removed
  3. washthe aqueous phase is washed with (C2H5)2O
  4. additionby addition of KHSO)4
  5. extractionit is then extracted in CH3COOC2H5

Sources & evidence

ORD record
ord-85fd4a2d47e949e5bfd97823967e2997
Source dataset
uspto-grants-1996_04
Patent number
US05506258

Reaction notes

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