Hydrochloric Acid → (2S)-2-[(4-Bromophenyl)(4-fluorophenyl)methoxy]-4-methylpentanoic acid

HRID 1180409Notes

Reaction equation

HRID 1180409 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[O:9][C@@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:11]([O:13]C)=[O:12])=[CH:4][CH:3]=1.Cl>CO.C1COCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[O:9][C@@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86605383Methyl (2S)-2-[(4-bromophenyl)(4-fluorophenyl)methoxy]-4-methylpentanoate

Product 1

HCID 69470167(2S)-2-[(4-Bromophenyl)(4-fluorophenyl)methoxy]-4-methylpentanoic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a suspension of methyl (2S)-2-[(4-bromophenyl)(4-fluorophenyl)methoxy]-4-methylpentanoate of step 3 (0.38 mmol, 157 mg) in MeOH/THF/H2O (1:2:2 mL) was added LiOH monohydrate (0.96 mmol, 40 mg). The mixture was stirred at r.t. for 2 h. HCl (1N) was added until pH 1. The mixture was extracted with CH2Cl2. The combined extracts were dried over anhydrous, MgSO4 and concentrated. The crude acid was used without further purification.

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. dry with materialThe combined extracts were dried over anhydrous, MgSO4
  3. concentrationconcentrated
  4. customThe crude acid was used without further purification

Sources & evidence

ORD record
ord-8131153c8dc64d439a2d4277b9357ccb
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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