Sodium Hydroxide → HCID 22237641, compound

HRID 1884756Notes

Reaction equation

HRID 1884756 reaction equation
C[O:2][C:3](=[O:49])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[C:19]([Br:20])=[CH:18][C:17]([C:21](=[O:37])[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:16][C:15]=2[C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=2)=[CH:6][C:5]=1[OH:48].[OH-].[Na+]>CCO>[Br:20][C:19]1[C:14]([O:13][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:49])=[O:2])=[C:5]([OH:48])[CH:6]=2)=[C:15]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=2)[CH:16]=[C:17]([C:21](=[O:37])[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 542003754-{2-[3-Bromo-5-(8-phenyl-octylcarbamoyl)-3'-trifluoromethyl-biphenyl-2-yloxy]-ethoxy}-2-hydroxy-benzoic acid methyl ester

Product 1

HCID 22237641HCID 22237641, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-{2-[3-Bromo-5-(8-phenyl-octylcarbamoyl)-3′-trifluoromethyl-biphenyl-2-yloxy]-ethoxy}-2-hydroxy-benzoic acid methyl ester (1.16 mmol, 1 eq) in EtOH (20 mL) was added 1M NaOH (10 mL) and the reaction was heated at reflux 90 min. It was then cooled to rt, concentrated in vacuo, diluted with H2O, and acidified with 2M HCl to pH 1. It was extracted with EtOAc, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (30% EtOAc:Hexane +1% Formic acid) to afford the title compound (0.607 g, 79%) as a white foam. 1H NMR (DMSO-d6) δ 13.55 (bs, 1H); 11.49 (bs, 1H); 8.58 (t, 1H); 8.14 (d, 1H); 7.90-7.84 (m, 3H); 7.73-7.61 (m, 3H); 7.26-7.12 (m, 5H); 6.27-6.23 (m, 2H); 4.00 (m, 2H); 3.92 (m, 2H); 3.23 (dd, 2H); 2.52 (t, 2H); 1.52 (m, 4H); 1.28 (m, 8H); IR (KBr) 3400, 2950, 2850, 1660, 1620, 1550, 1450, 1420, 1330, 1220, 1160, 1120 cm−1; mass spectrum [(−)ESI], m/z 726/728 (M−H)−; Anal. Calcd. for C37H37F3NO6: C, 60.99; H, 5.12; N, 1.92, Found: C, 60.32; H, 5.17; N, 1.83.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux 90 min
  3. concentrationconcentrated in vacuo
  4. additiondiluted with H2O
  5. extractionIt was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (30% EtOAc:Hexane +1% Formic acid)

Sources & evidence

ORD record
ord-8bdc65d66ecb4d2bae8633ca036954cb
Source dataset
uspto-grants-2004_07
Patent number
US06765021B2

Reaction notes

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