Trifluoroacetic acid → HCID 86655024, compound

HRID 2066899Notes

Reaction equation

HRID 2066899 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])=[CH:23][C:22]=3[F:36])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28][C:29]([OH:31])=[O:30])=[CH:23][C:22]=3[F:36])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86655025HCID 86655025, compound

Product 1

HCID 86655024HCID 86655024, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[1-(4-tert-Butoxycarbonylmethyl-2,5-difluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester 75a (368 mg) was dissolved in DCM (5 mL) and TFA (3 mL) and stirred at r.t. for 4 h. The solvent was removed in vacuo, DCM and water were added and the organic phase was dried over MgSO4 and concentrated to give 4-[1-(4-carboxymethyl-2,5-difluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester 75b (300 mg).

Workup

  1. customThe solvent was removed in vacuo, DCM and water
  2. additionwere added
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9bc2836f5d1c4e54ba17b55ce4d63371
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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