Potassium Carbonate → Benzyl 2-(3-amino-1,2,4-thiadiazol-5-YL)pyrrolidine-1-carboxylate

HRID 1170514Notes

Reaction equation

Br.[CH2:2]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]1[S:21][N:20]=[C:19]([NH:22]C(=O)C)[N:18]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[CH2:2]([O:9][C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]1[S:21][N:20]=[C:19]([NH2:22])[N:18]=1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(3-Acetylamino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester hydrobromide (14.0 g, 37.8 mmol) was dissolved in ethanol (80 mL). The reaction mixture was cooled to 0° C. and a solution of K2CO3 (15.0 g, 108.7 mmol) in H2O (40 mL) was added. The solution was allowed to return to room temperature while stirring for 30 mins. The solution was concentrated down, redissolved in water (100 mL) and extracted with DCM (3×50 mL). The organic layers were combined and washed with brine (3×50 mL). The organic layer was partitioned from the aqueous layer, dried over MgSO4 and concentrated under vacuo to afford 9.4 g (94%) of 2-(3-amino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester as a yellow oil.

Workup

customto return to room temperature
concentrationThe solution was concentrated down
dissolutionredissolved in water (100 mL)
extractionextracted with DCM (3×50 mL)
washwashed with brine (3×50 mL)
customThe organic layer was partitioned from the aqueous layer
dry with materialdried over MgSO4
concentrationconcentrated under vacuo

Sources & evidence

ORD record: ord-52e89bc613294643ba254eabd0ffe2bc
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825256B2

Reaction notes

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