Hydrochloric Acid → 3-[({[6-Fluoro-3'-(hydroxymethyl)-3-biphenylyl]methyl}amino)carbonyl]benzoic acid

HRID 564489Notes

Reaction equation

HRID 564489 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[CH:9]=2)=[CH:6][C:5]([CH2:16][NH:17][C:18]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25]C)=[O:24])=[O:19])=[CH:4][CH:3]=1.[OH-].[Li+].C1COCC1.Cl>O>[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[CH:9]=2)=[CH:6][C:5]([CH2:16][NH:17][C:18]([C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([OH:25])=[O:24])=[O:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57813353Methyl 3-[({[6-fluoro-3'-(hydroxymethyl)-3-biphenylyl]methyl}amino)-carbonyl]benzoate

Product 1

HCID 578135113-[({[6-Fluoro-3'-(hydroxymethyl)-3-biphenylyl]methyl}amino)carbonyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 3-[({[6-fluoro-3′-(hydroxymethyl)-3-biphenylyl]methyl}amino)-carbonyl]benzoate (0.309 g, 0.786 mmol), lithium hydroxide (0.0282 g, 1.2 mmol), THF (6 mL), and water (2 mL) were combined and stirred under argon at room temperature overnight. Solvents were pumped off, the residue adjusted to pH 2 with 1N HCl, and extracted with EtOAc, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford the title compound as a white solid. LC-MS m/z 379.8 (M+H)+, 1.69 min (ret time); mp 169-171° C.; analytical HPLC shows 93.2% purity, (ret time 7.059 min).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a3f3a7a22b1048aa8613c707d16a3c90
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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