Methanol → HCID 22051116, compound

HRID 1867186Notes

Reaction equation

HRID 1867186 reaction equation
[Br:1][C:2]1[C:3](=[O:30])[N:4]([C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][C:20]=2[F:29])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].CO.O.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[C:3](=[O:30])[N:4]([C:19]2[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=2[F:29])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 22051019HCID 22051019, compound

Product 1

HCID 22051116HCID 22051116, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound of Example 604 (4.1 g, 8.5 mmol) was suspended in tetrahydrofuran (30 mL), methanol (15 mL), water (15 mL) and 2.5 N NaOH (6.8 mL, 17 mmol)). After stirring at room temperature for 2 hour, the reaction was complete and the organics were removed. The aqueous layer was acidified to pH 1 with 3N HCl, the solids were suspended in water, filtered, and washed with diethyl ether. The title compound was obtained as a white powder and used without further purification (4.4 g). 1H NMR (400 MHz, CD3OD) δ 8.00 (dd, J=1.8 and 8.8 Hz, 1H), 7.93 (dd, J=1.48 and 10 Hz, 1H), 7.64 (q, J=8 and 14.8 Hz, 1H), 7.49 (t, J=7.6 Hz, 1H), 7.05 (t, J=10 Hz, 2H), 6.66 (s, 1H), 5.36 (s, 2H), 2.08 (s, 3H) ppm. 19F NMR (400 MHz, CD3OD) δ −111.48 (1F), −115.96 (1F), −123.35 (1F) ppm. ES-HRMS m/z 468.9987 (M+H calcd for C20H14BrF3NO4 requires 469.0086).

Workup

  1. customthe organics were removed
  2. filtrationfiltered
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-83b25865f0244c68a3a7a6ff9e65d74b
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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