Hydrochloric Acid → 4-(4-Fluoro-3,5-diisopropoxybenzamido)benzoic acid

HRID 62776ノート

反応式

HRID 62776 の反応式
[F:1][C:2]1[C:20]([O:21][CH:22]([CH3:24])[CH3:23])=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[O:25][CH:26]([CH3:28])[CH3:27].[Li+].[OH-].Cl>C1COCC1>[F:1][C:2]1[C:3]([O:25][CH:26]([CH3:27])[CH3:28])=[CH:4][C:5]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=2)=[O:7])=[CH:19][C:20]=1[O:21][CH:22]([CH3:24])[CH3:23]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67041964HCID 67041964、化合物

生成物 1

HCID 670417944-(4-Fluoro-3,5-diisopropoxybenzamido)benzoic acid収率 38%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of methyl 4-(4-fluoro-3,5-diisopropoxybenzamido)benzoate (10) (32 mg, 51% purity, 82 μmol) in THF (1 mL) and 2M LiOH (0.16 mL, 0.33 mmol) was stirred at RT for 20 h, then at 45° C. for 2 h. The mixture was allowed to cool to RT and was acidified by the addition of 1M HCl. The mixture was partitioned between EtOAc (10 mL) and water (10 mL) and the phases were separated. The organic solution was washed with brine (3× mL), then dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by reverse phase HPLC to afford 4-(4-fluoro-3,5-diisopropoxybenzamido)benzoic acid (AAA-119) (8 mg, 38%) as a white solid: m/z 376 [M+H]+ (ES+), 374 [M−H]− (ES−); 1H NMR (400 MHz, DMSO-d6) δ: 10.37 (1H, s), 7.93 (2H, d), 7.83 (2H, d), 7.35 (2H, d), 4.73 (2H, sep), 1.32 (12H, d). NB acid proton not visible.

後処理

  1. waitat 45° C. for 2 h
  2. temperatureto cool to RT
  3. customThe mixture was partitioned between EtOAc (10 mL) and water (10 mL)
  4. customthe phases were separated
  5. washThe organic solution was washed with brine (3× mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-e8b96f9730234de7bc3e3f2e85e978ba
出典データセット
uspto-grants-2016_09
特許番号
US09447028B2

反応ノート

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