Trifluoroacetic acid → HCID 69655848, compound

HRID 857733Notes

Reaction equation

HRID 857733 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([OH:29])([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[C:9]([N:11]2[CH2:22][CH2:21][CH2:20][C@H:12]2[C:13]([O:15]C(C)(C)C)=[O:14])=[O:10])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([OH:29])([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[C:9]([N:11]2[CH2:22][CH2:21][CH2:20][C@H:12]2[C:13]([OH:15])=[O:14])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69656634HCID 69656634, compound

Product 1

HCID 69655848HCID 69655848, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The nonpolar isomer tert-butyl 1-[(3-chlorophenyl)(hydroxy)pyridin-3-ylacetyl]-L-prolinate (0.087 g, 0.21 mmol) was dissolved in dichloromethane (4 mL) and trifluoroacetic acid (1 mL) and stirred at room temperature for 4 hours. Then the mixture was evaporated in vacuo and vacuum dried to yield the nonpolar isomer of 1-[(3-chlorophenyl)(hydroxy)pyridin-3-ylacetyl]-L-proline (0.04 g, HPLC RT=2.51 min, Method A; LCMS m/z=361).

Workup

  1. customThen the mixture was evaporated in vacuo and vacuum
  2. customdried

Sources & evidence

ORD record
ord-c7b7ddfcaff746aebde74ae0c107c958
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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