Trifluoroacetic acid → HCID 178501207, compound

HRID 2279329Notes

Reaction equation

HRID 2279329 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([NH:18]C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)=[O:11]>ClCCl>[CH3:8][O:9][C:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([NH2:18])[CH2:14][CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178501239HCID 178501239, compound

Product 1

HCID 178501207HCID 178501207, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (13.47 mL, 19.94 mmol, 15.0 eq) is added at 0° C. to a stirred solution of trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid methyl ester (3.53 g, 11.66 mmol, 1.0 eq) in dichloromethane (100 mL). After 15 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×50 mL) and water (50 mL) and the pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford trans-4-amino-cyclohexanecarboxylic acid methyl ester as a yellow oil (1.53 g, 79% yield).

Workup

  1. extractionthe reaction mixture is extracted with dichloromethane (3×50 mL) and water (50 mL)
  2. additionthe pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-671cb743bef24a6faa3a9bd4a342b058
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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