Trifluoroacetic acid → (R)-2-Amino-3-cyclohexylpropanoic acid trifluoroacetate

HRID 1943297Notes

Reaction equation

HRID 1943297 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C([NH:15][C@H:16]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:17]([OH:19])=[O:18])(OC(C)(C)C)=O>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[NH2:15][C@H:16]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 2755927(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-cyclohexylpropanoic acid

Product 1

HCID 68547671(R)-2-Amino-3-cyclohexylpropanoic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 ml of TFA were added to a solution of (R)-N-Boc-2-amino-3-cyclohexylpropanoic acid (3.0 g, 11.1 mmol) in 20 ml of CH2Cl2, and the mixture was stirred at RT overnight. After deprotection was complete, the CH2Cl2 was evaporated off, and the remaining solid was mixed with 50 ml of H2O and lyophilized. Yield: 2.84 g (90%) of (R)-2-amino-3-cyclohexylpropanoic acid trifluoroacetate as colorless solid.

Workup

  1. customthe CH2Cl2 was evaporated off
  2. additionthe remaining solid was mixed with 50 ml of H2O

Sources & evidence

ORD record
ord-e1635b8dee454b27a6afff92f3283f61
Source dataset
uspto-grants-2013_03
Patent number
US08389764B2

Reaction notes

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