Sodium Hydroxide → HCID 22237641, compound

HRID 324128Notes

Reaction equation

HRID 324128 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 54200375HCID 54200375, compound

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) δ13.55 (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-70ef44cc86084f4d80fe992e9262cffe
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Reaction notes

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