Hydrochloric Acid → HCID 57512782, compound

HRID 2071173Notes

Reaction equation

HRID 2071173 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=2)[C:17]([O:19]C)=[O:18])=[O:13])[S:5][CH:6]=1.[Li+].[OH-].Cl>C1COCC1.O>[CH3:1][C:2]1[N:3]=[C:4]([C@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=2)[C:17]([OH:19])=[O:18])=[O:13])[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57512781HCID 57512781, compound

Product 1

HCID 57512782HCID 57512782, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of (R)-methyl 3-(2-(4-methylthiazol-2-yl)pyrrolidine-1-carbonyl)benzoate (155 mg, 0.49 mmol) in THF (5 mL) was added 1N LiOH (2 mL) and the reaction mixture was stirred at rt for 1 h. Then the volatiles were removed on a rotavap under reduced pressure. Then reaction mixture was diluted with water, acidified with 1N HCl to pH ˜3 and extracted with ethyl acetate. Organic layer was dried and evaporated to yield 132 mg of the acid (R)-3-(2-(4-methylthiazol-2-yl)pyrrolidine-1-carbonyl)benzoic acid. \

Workup

  1. customThen the volatiles were removed on a rotavap under reduced pressure
  2. customThen reaction mixture
  3. extractionextracted with ethyl acetate
  4. customOrganic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-c4a7e740623048e395fdda1fded5daad
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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