Carbon Dioxide → 5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid

HRID 546391Notes

Reaction equation

HRID 546391 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[CH:15][S:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](=[O:19])=[O:18].[OH-].[Na+].C(OCC)C>O1CCCC1.C([Li])CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15]([C:17]([OH:19])=[O:18])[S:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 17842404tert-Butyl 6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)-carboxylate

Product 1

HCID 113237345-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 178418339ButyllithiumSolvent

Procedure

To a solution of 5-tert-butoxycarbonyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (845 mg) in absolute tetrahydrofuran (20 ml), n-butyllithium (1.65N hexane solution, 2.13 ml) was added dropwise at −78° C., and the mixture was stirred for 30 minutes with ice cooling. After passing carbon dioxide gas into the reaction mixture at −78° C. for 1 hour, the reaction mixture was warmed to room temperature. A 5N aqueous solution of sodium hydroxide and diethyl ether were added to the reaction mixture to separate a water layer. 6N Hydrochloric acid was added to the water layer to adjust the pH thereof to 1 to 2. After addition of dichloromethane, an organic layer separated was washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (562 mg) as a pale yellow foamy substance.

Workup

  1. customat −78° C.
  2. customfor 1 hour
  3. customto separate a water layer
  4. addition6N Hydrochloric acid was added to the water layer
  5. additionAfter addition of dichloromethane
  6. customan organic layer separated
  7. washwas washed with saturated saline
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f47c334d6fb944ec890ac67a6d0eebfc
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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