Hydrochloric Acid → (3S,4S)-1-((tert-Butoxy)carbonyl)pyrrolidine-3,4-dicarboxylic acid

HRID 1987170Notes

Reaction equation

HRID 1987170 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:10]([C:11]([O:13]CC)=[O:12])[CH2:9][N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Na+].[Cl-]>C1COCC1.O>[C:19]([O:18][C:16]([N:8]1[CH2:7][C@@H:6]([C:4]([OH:5])=[O:3])[C@H:10]([C:11]([OH:13])=[O:12])[CH2:9]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 59512444(3R,4R)-1-tert-butyl 3,4-diethyl pyrrolidine-1,3,4-tricarboxylate

Product 1

HCID 69651971(3S,4S)-1-((tert-Butoxy)carbonyl)pyrrolidine-3,4-dicarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 1b (1 g, 3.17 mmol) was dissolved in of THF (8 ml), and 80 mL of water was added. The reaction mixture was immersed in an ice-water bath and cooled to 0 C. To this reaction mixture, 96 ml of 0.25 N NaOH was added in small portions with stirring until the consumption of the starting diester was detected by thin-layer chromatography. The reaction was stirred at the same temperature for about 30 min to 1 h, and the reaction mixture was acidified with 1 N HCl at 0° C., saturated with NaCl, extracted with ethyl acetate four times (each 100 ml), and dried with sodium sulfate. The organic phase is evaporated to dryness and dried in vacuo. Yield: 0.68 g (82.7%), ESI-MS: m/z=258 [M−H]−

Workup

  1. additionwas added
  2. customThe reaction mixture was immersed in an ice-water bath
  3. temperaturecooled to 0 C
  4. extractionextracted with ethyl acetate four times (each 100 ml), and
  5. dry with materialdried with sodium sulfate
  6. customThe organic phase is evaporated to dryness
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8d683187c8234af3aec4ac1416427988
Source dataset
uspto-grants-2009_06
Patent number
US07550487B2

Reaction notes

Loading…