Sodium Methoxide → HCID 67289561, compound

HRID 1626518Notes

Reaction equation

HRID 1626518 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:34])[NH:20][CH2:21][CH2:22][C:23]3[C:24]([O:32][CH3:33])=[N:25][C:26]([CH:29]4[CH2:31][CH2:30]4)=[CH:27][CH:28]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([OH:37])=[O:36].C[O-].[Na+:40]>CO>[Na+:40].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:34])[NH:20][CH2:21][CH2:22][C:23]3[C:24]([O:32][CH3:33])=[N:25][C:26]([CH:29]4[CH2:31][CH2:30]4)=[CH:27][CH:28]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([O-:37])=[O:36]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67287710HCID 67287710, compound

Product 1

HCID 67289561HCID 67289561, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Chloro-7-(4-(2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid (70 mg, 0.13 mmol) was diluted with methanol (1 mL) followed by the addition of NaOMe (268 μL, 0.13 mmol). After stirring for 2 hours, the reaction was concentrated and dried under high vacuum pressure for 2 hours. The material was diluted with hexanes, sonicated and concentrated to afford 6-chloro-7-(4-(2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethylcarbamoyl)phenoxy)chroman-4-carboxylic acid sodium salt (40 mg, 0.076 mmol, 57% yield). MS (es+apci, positive) m/z=523.2.]

Workup

  1. concentrationthe reaction was concentrated
  2. customdried under high vacuum pressure for 2 hours
  3. additionThe material was diluted with hexanes
  4. customsonicated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-55b284a821ae47e1b1952e19dd81703e
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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