Lithium Hydroxide → 1-(4-Phenylthiazol-2-yl)pyrrolidine-3-carboxylic acid

HRID 874945Notes

Reaction equation

HRID 874945 reaction equation
[OH-].[Li+].[C:3]1([C:9]2[N:10]=[C:11]([N:14]3[CH2:18][CH2:17][CH:16]([C:19]([O:21]C)=[O:20])[CH2:15]3)[S:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1.O>[C:3]1([C:9]2[N:10]=[C:11]([N:14]3[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=[O:20])[CH2:15]3)[S:12][CH:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67323747Methyl 1-(4-phenylthiazol-2-yl)pyrrolidine-3-carboxylate

Product 1

HCID 630313291-(4-Phenylthiazol-2-yl)pyrrolidine-3-carboxylic acidYield 56.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (10 mg, 0.39 mmol) was added to a solution of methyl 1-(4-phenylthiazol-2-yl)pyrrolidine-3-carboxylate (75 mg, 0.26 mmol) in THF-H2O (3 mL, 7:3 v/v) at 0° C. The reaction mixture was allowed to warm up to room temperature, stirred for 1 h, concentrated under reduced pressure, and then diluted with water. The aqueous layer was washed with EtOAc. The pH of the aqueous layer was adjusted to ˜3 using 1.5N HCl and the organic product was extracted with EtOAc. The combined extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 1-(4-phenylthiazol-2-yl)pyrrolidine-3-carboxylic acid (40 mg, yield 56%) as off-white solid, which was carried through without further purification. MS (ESI) m/z: Calculated for C14H14N2O2S: 274.08. found: 275.0 (M+H)+

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with water
  3. washThe aqueous layer was washed with EtOAc
  4. extractionthe organic product was extracted with EtOAc
  5. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e80b832a3fa4e79bd00c244f535b9d8
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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