Water → HCID 178522239, compound

HRID 572229Notes

Reaction equation

HRID 572229 reaction equation
C([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C@H:12]2[CH2:17][CH2:16][C@@H:15]([NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)=[O:20])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)C.[OH-].[Li+].O>CC#N>[F:30][C:29]([F:31])([F:32])[O:28][C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:19](=[O:20])[NH:18][C@@H:15]2[CH2:16][CH2:17][C@H:12]([O:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:33])=[O:3])=[CH:10][CH:9]=3)[CH2:13][CH2:14]2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 178469090HCID 178469090, compound

Product 1

HCID 178522239HCID 178522239, compoundYield 912.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 19b (0.1 g, 0.21 mmol) in 5 mL of CH3CN was added lithium hydroxide (15.4 mg, 0.64 mmol) followed by 2 mL of water at room temperature. The reaction mixture was stirred overnight. The solvent was evaporated in vacuo and washed with EtOAc. The aqueous layer was acidified with 1N HCl to give white precipitates. The resulting white solids were collected by suction filtration and washed with water. The crude product was recrystallized from MeOH to give the titled compound (0.84 g, 90%) as a white solid. mp 210-212° C. 1H NMR (DMSO-d6): 12.60 (s, 1H), 8.48 (s, 1H), 7.87 (d, J=8 Hz, 1H), 7.47 (d, J=9 Hz, 1H), 7.21 (d, J=9 Hz, 1H), 7.03 (d, J=8 Hz, 1H), 6.35 (d, J=8 Hz, 1H), 4.66-4.57 (m, 1H), 3.73-3.60 (m, 1H), 1.87-1.50 (m, 1H). 13C NMR (DMSO-d6): □ 167.04, 160.90, 154.36, 141.99, 139.84, 131.48, 122.77, 121.67, 118.57, 115.28, 71.95, 45.66, 27.71, 27.36. MS (ESI) m/z: 439.1 (M+H+). Anal. Calcd for C21H21F3N2O5: C, 57.53; H, 4.83; N, 6.39. Found: C, 57.33; H, 4.81; N, 6.29.

Workup

  1. customThe solvent was evaporated in vacuo
  2. washwashed with EtOAc
  3. customto give white precipitates
  4. filtrationThe resulting white solids were collected by suction filtration
  5. washwashed with water
  6. customThe crude product was recrystallized from MeOH

Sources & evidence

ORD record
ord-c5b47f1740084177b2059ef61b702404
Source dataset
uspto-grants-2015_05
Patent number
US09029401B2

Reaction notes

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