Trifluoroacetic acid → 3-cyclohexyl-(L)-alanine phenylmethyl ester trifluoroacetate

HRID 568116Notes

Reaction equation

HRID 568116 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:26])[C@H:10]([CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[NH:11]C(OC(C)(C)C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30]>ClCCl>[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[C:1]1([CH2:7][O:8][C:9](=[O:26])[C@H:10]([CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53857713N-[(1,1-dimethylethoxy)carbonyl]-3-cyclohexyl-(L)-alanine phenylmethyl ester

Product 1

HCID 700214063-cyclohexyl-(L)-alanine phenylmethyl ester trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 35.3 g (94.5 mmole) of N-[(1,1-dimethylethoxy)carbonyl]-3-cyclohexyl-(L)-alanine phenylmethyl ester in 100 mL of dichloromethane at 17° C. is added 100 mL of trifluoroacetic acid over 15 minutes during which time the reaction mixture temperature rises to 21° C. The reaction mixture is stirred overnight, then is concentrated in vacuo. The residue is azeotroped with dichloromethane, toluene and methyl tert-butyl ether. The resulting oil is subjected to high vacuum to afford 3-cyclohexyl-(L)-alanine phenylmethyl ester trifluoroacetate (32.6 g). MS (ion spray) m/z 262 (M+H)+.

Workup

  1. customrises to 21° C
  2. concentrationis concentrated in vacuo
  3. customThe residue is azeotroped with dichloromethane, toluene and methyl tert-butyl ether

Sources & evidence

ORD record
ord-101a511fef3c4fe788c42500d6277cf3
Source dataset
uspto-grants-2001_01
Patent number
US06180759B2

Reaction notes

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