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Hydrochloric Acid → (R)-3-pyrrolidin-3-yl-4H-[1,2,4]thiadiazol-5-one

HRID 1040419
Notes
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Reaction equation

HRID 1040419 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[NH:17][C:16](=[O:18])[S:15][N:14]=2)[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>CO>[NH:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[NH:17][C:16](=[O:18])[S:15][N:14]=2)[CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 136383467(R)-3-(5-oxo-4,5-dihydro-[1,2,4]thiadiazol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 136383465(R)-3-pyrrolidin-3-yl-4H-[1,2,4]thiadiazol-5-oneYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-3-(5-Oxo-4,5-dihydro-[1,2,4]thiadiazol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (420 mg, 1.55 mmol) was dissolved in methanol (15 mL). 4M HCl in dioxane (0.70 mL, 2.80 mmol) was then added. The solution was stirred overnight. The reaction was concentrated in vacuo. The residue was purified by reverse phase HPLC to afford (R)-3-pyrrolidin-3-yl-4H-[1,2,4]thiadiazol-5-one (220 mg, 1.28 mmol, 83%) as a white solid.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-926a9de67ad74b1491ce8ad56a12db9e
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08552205B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes