Sodium Hydroxide → [4-({(2-Cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetic acid

HRID 1269685ノート

反応式

HRID 1269685 の反応式
[CH:1]1([CH2:4][CH2:5][N:6]([C:24]2[CH:25]=[C:26]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)[CH:27]=[CH:28][CH:29]=2)[S:7]([C:10]2[CH:22]=[CH:21][C:13]([O:14][CH2:15][C:16]([O:18]CC)=[O:17])=[C:12]([CH3:23])[CH:11]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1.[OH-].[Na+]>CO.C1COCC1>[CH:1]1([CH2:4][CH2:5][N:6]([C:24]2[CH:25]=[C:26]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:37])[F:38])=[CH:32][CH:31]=3)[CH:27]=[CH:28][CH:29]=2)[S:7]([C:10]2[CH:22]=[CH:21][C:13]([O:14][CH2:15][C:16]([OH:18])=[O:17])=[C:12]([CH3:23])[CH:11]=2)(=[O:9])=[O:8])[CH2:2][CH2:3]1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 58622892Ethyl [4-({(2-cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate

生成物 1

HCID 18448285[4-({(2-Cyclopropylethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetic acid収率 43.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl [4-({(2-cyclopropylethyl)[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amino}sulfonyl)-2-methylphenoxy]acetate (156 mg, 0.28 mmol) in MeOH (2 mL) and THF (2 mL) at room temperature was added 2M NaOH aq. (1 mL, 2 mmol). The resultant mixture was stirred for 2 h. The solvents were removed in vacuo and the residue was partitioned between EtOAc (2×20 mL) and 2M HCl (20 mL). The organic solution was dried (MgSO4) and the solvent was removed in vacuo. Purification by SPE (5 g aminopropyl cartridge), loading crude material in CH2Cl2 and then washing with MeOH, prior to eluting with 5% NH3 in MeOH. The 5% NH3 in MeOH extract was concentrated in vacuo and the residue was partitioned between CH2Cl2 (20 mL) and 2M HCl (2 mL). The organic solution was dried (MgSO4) and the solvent was removed in vacuo affording the title compound as a white solid (64.4 mg).

後処理

  1. customThe solvents were removed in vacuo
  2. customthe residue was partitioned between EtOAc (2×20 mL) and 2M HCl (20 mL)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customPurification by SPE (5 g aminopropyl cartridge)
  6. washwashing with MeOH
  7. washto eluting with 5% NH3 in MeOH
  8. extractionThe 5% NH3 in MeOH extract
  9. concentrationwas concentrated in vacuo
  10. customthe residue was partitioned between CH2Cl2 (20 mL) and 2M HCl (2 mL)
  11. dry with materialThe organic solution was dried (MgSO4)
  12. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-66115209ce2b47649b1d4924c75e8fb7
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

反応ノート

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