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

HRID 62776노트

반응식

HRID 62776 반응식
[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]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67041964HCID 67041964, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e8b96f9730234de7bc3e3f2e85e978ba
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447028B2

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