Hydrochloric Acid → HCID 9875633, compound

HRID 1281464Notes

Reaction equation

HRID 1281464 reaction equation
C[O:2][C:3](=[O:58])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[CH:18][C:17]([C:30](=[O:46])[NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:16][C:15]=2[C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([C:53]([F:56])([F:55])[F:54])[CH:48]=2)=[CH:6][C:5]=1[OH:57].[OH-].[Na+].Cl>CCO.O>[OH:57][C:5]1[CH:6]=[C:7]([O:10][CH2:11][CH2:12][O:13][C:14]2[C:15]([C:47]3[CH:52]=[CH:51][CH:50]=[C:49]([C:53]([F:54])([F:55])[F:56])[CH:48]=3)=[CH:16][C:17]([C:30](=[O:46])[NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:18][C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=2)[CH:8]=[CH:9][C:4]=1[C:3]([OH:58])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86583672HCID 86583672, compound

Product 1

HCID 9875633HCID 9875633, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-hydroxy-4-{2-[5′-(8-phenyl-octylcarbamoyl)-3,3″-bis-trifluoromethyl[1,1′;3′,1″]terphenyl-2′-yloxy]-ethoxy}-benzoic acid methyl ester (0.980 g, 1.21 mmol, 1 eq) in EtOH (20 mL) was added 50% NaOH (10 mL) and the reaction was heated at reflux overnight. It was cooled to rt, 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) to afford the title compound (0.92 g, 96%) as a white foam. 1H NMR (DMSO-d6) δ 13.60 (bs, 1H); 11.40 (bs, 1H); 8.59 (bt, 1H); 8.00-7.92 (m, 6H); 7.74-7.65 (m, 4H); 7.56 (d, 1H); 7.25-7.10 (m, 5H); 6.08-6.00 (m, 2H); 3.66 (bd, 2H); 3.52 (bd, 2H); 3.25 (dd, 2H); 2.52 (t, 2H); 1.53 (m, 4H); 1.27 (m, 8H); IR (KBr) 3350, 2950, 2850, 1670, 1620, 1550, 1500, 1460, 1320, 1230, 1220, 1160, 1120, 1095, cm−1; mass spectrum [(−)APCI], m/z 792 (M−H)−; Anal. Calcd. for C44H41F6NO6: C, 66.58; H, 5.21; N, 1.76, Found: C, 64.86; H, 5.22; N, 1.68.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux overnight
  3. extractionIt was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (30% EtOAc:hexane)

Sources & evidence

ORD record
ord-806990042d514b39b84c1809c058c64c
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

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