Sodium Hydroxide → 2-(4-(4-(3,4-Dichlorobenzamido)phenoxy)-3-((4-fluorophenylsulfonamido)methyl)-phenyl)acetic acid

HRID 1927715Notes

Reaction equation

HRID 1927715 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][C:40]=1[Cl:41])[C:5]([NH:7][C:8]1[CH:37]=[CH:36][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]C)=[O:21])=[CH:15][C:14]=2[CH2:24][NH:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[CH:10][CH:9]=1)=[O:6].[OH-].[Na+]>CO.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:38]=[CH:39][C:40]=1[Cl:41])[C:5]([NH:7][C:8]1[CH:37]=[CH:36][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][C:14]=2[CH2:24][NH:25][S:26]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)(=[O:27])=[O:28])=[CH:10][CH:9]=1)=[O:6]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 68463196Methyl 2-(4-(4-(3,4-dichlorobenzamido)phenoxy)-3-((4-fluorophenyl-sulfonamido)methyl)phenyl)acetate

Product 1

HCID 247437562-(4-(4-(3,4-Dichlorobenzamido)phenoxy)-3-((4-fluorophenylsulfonamido)methyl)-phenyl)acetic acidYield 30.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(4-(4-(3,4-dichlorobenzamido)phenoxy)-3-((4-fluorophenyl-sulfonamido)methyl)phenyl)acetate (40 mg, 0.065 mmol) was diluted with MeOH (1 mL) followed by the addition of NaOH (0.32 mL, 1.3 mmol). After stirring for 1 hour, the reaction mixture was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a 0.5 mm preparative plate eluting with methylene chloride:MeOH:AcOH (90:9:1) to yield 12 mg of the title compound as a solid. 1H NMR (400 MHz, CDCl3/CD3OD) 8.1 (m, 1H), 7.85 (m, 1H), 7.8 (m, 2H), 7.7 (d, 1H), 7.6 (d, 1H), 7.25 (s, 1H), 7.2 (m, 3H), 6.85 (d, 2H), 6.7 (d, 1H), 4.15 (s, 2H), 3.55 (s, 2H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe material was purified
  6. washeluting with methylene chloride:MeOH:AcOH (90:9:1)

Sources & evidence

ORD record
ord-ae36002c91ea4a99869041531e6658b5
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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