Methanol → HCID 67287941, compound

HRID 1626447Notes

Reaction equation

HRID 1626447 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:35])[NH:20][CH2:21][CH2:22][C:23]3[C:24]([O:33][CH3:34])=[N:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:36]([OH:38])=[O:37].C[O-].[Na+:41].CO>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:35])[NH:20][CH2:21][CH2:22][C:23]3[C:24]([O:33][CH3:34])=[N:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:36]([O-:38])=[O:37].[Na+:41]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 67287942HCID 67287942, compound

Product 1

HCID 67287941HCID 67287941, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

6-Chloro-7-(4-(2-(2-methoxy-6-(trifluoromethyl)pyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid (255 mg, 0.463 mmol) in 2:1 THF-MeOH (2 ml) was treated with 0.5 N sodium methoxide in methanol (926 μl, 0.463 mmol) at ambient temperature. After 15 minutes, the reaction was concentrated in vacuo. The material was suspended in ethyl acetate and concentrated to a solid. The solid was suspended in ethyl acetate, hexanes were added, and the mixture was concentrated in vacuo to a solid. The material was suspended in dichloromethane, hexanes were added, and the suspension concentrated to provide the desired compound (268 mg, 0.468 mmol, 101% yield) as a solid. MS (apci) m/z=551.0 (M-Na+2H).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. concentrationconcentrated to a solid
  3. additionhexanes were added
  4. concentrationthe mixture was concentrated in vacuo to a solid
  5. additionhexanes were added
  6. concentrationthe suspension concentrated

Sources & evidence

ORD record
ord-c002ad68449442d3bceefec213fd7f47
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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