Sodium Hydroxide → 4-Methyl-2-(2-phenylthiazol-4-yl)pentanoic acid

HRID 1060741Notes

Reaction equation

HRID 1060741 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]([C:10]1[N:11]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[S:13][CH:14]=1)[C:5]([O:7]CC)=[O:6].[OH-].[Na+]>CO>[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]([C:10]1[N:11]=[C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[S:13][CH:14]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 18628735Ethyl 4-methyl-2-(2-phenylthiazol-4-yl)pentanoate

Product 1

HCID 110766664-Methyl-2-(2-phenylthiazol-4-yl)pentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution comprised of the ethyl 4-methyl-2-(2-phenylthiazol-4-yl)pentanoate in methanol (5 mL) was treated with sodium hydroxide (0.1 gm, 2 mmol). The mixture was stirred for 4 hours, basified with 0.1 M sodium hydroxide solution, washed with ethyl acetate (10 mL), acidified and extracted with ethyl acetate (50 mL). The extract was washed with water, dried (MgSO4) and concentrated. Product was purified from the residue by flash chromatography on silica gel (60° A) with 33% ethyl acetate in hexane as an eluent to provide 4-methyl-2-(2-phenylthiazol-4-yl)pentanoic acid (200 mg, 1.44 mmol). Rf 0.41. 1H NMR (DMSO-d6): 1.01 (m, 6H), 1.61-1.79 (m, 3H), 3.63 (m, 1H), 7.04 (d, 1H), 7.22-7.34 (m, 5H). LCMS: 276.1 (M+H+).

Workup

  1. washwashed with ethyl acetate (10 mL)
  2. extractionextracted with ethyl acetate (50 mL)
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customProduct was purified from the residue by flash chromatography on silica gel (60° A) with 33% ethyl acetate in hexane as an eluent

Sources & evidence

ORD record
ord-aa95c1d0df4d472289e746f25d40dd93
Source dataset
uspto-grants-2003_02
Patent number
US06525036B2

Reaction notes

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