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

HRID 453484ノート

反応式

HRID 453484 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-544e3bceaafc4da99bd788a2fd7c532b
出典データセット
uspto-grants-2013_07
特許番号
US08492437B2

反応ノート

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