HCID 178449822, compound → HCID 178449783, compound

HRID 2290001Notes

Reaction equation

HRID 2290001 reaction equation
C(OC([NH:8][CH:9]([CH:39]([CH3:41])[CH3:40])[C:10]([O:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[C:18]2[C:23](=[C:24]([F:26])[CH:25]=1)[N:22]=[CH:21][C:20]([C:27]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)=[O:28])=[C:19]2[OH:38])=[O:11])=O)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[NH2:8][CH:9]([CH:39]([CH3:41])[CH3:40])[C:10]([O:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[C:18]2[C:23](=[C:24]([F:26])[CH:25]=1)[N:22]=[CH:21][C:20]([C:27]([NH:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1)=[O:28])=[C:19]2[OH:38])=[O:11]

Participants

4

Reactant 1

HCID 178449822HCID 178449822, compound

Product 1

HCID 178449783HCID 178449783, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3-(3-{[(4-Chlorobenzyl)amino]carbonyl}-8-fluoro-4-hydroxy-6-quinolinyl)propyl 2-[(tert-butoxycarbonyl)amino]-3-methylbutanoate from Example No. 146 (0.13 g) is stirred in a mixture of 4 mL trifluoroacetic acid and 7 mL CH2Cl2 at 0° C. for approximately 1.5 h. Once the reaction is complete, the mixture is partitioned between CH2Cl2 and saturated NaHCO3. After the TFA is neutralized, any undissolved material is filtered off. The organic layer is washed once with water. The combined aqueous layers are back-extracted with CH2Cl2 and EtOAc. The organics are combined, dried over Na2SO4, filtered, and concentrated in vacuo to give a white solid. The solid is recrystallized from a minimal amount of EtOH. (0.040 g, 0.082 mmol, 35%).

Workup

  1. customthe mixture is partitioned between CH2Cl2 and saturated NaHCO3
  2. filtrationany undissolved material is filtered off
  3. washThe organic layer is washed once with water
  4. extractionThe combined aqueous layers are back-extracted with CH2Cl2 and EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a white solid
  9. customThe solid is recrystallized from a minimal amount of EtOH

Sources & evidence

ORD record
ord-af90d8647526499a80ac575571a6ceef
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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