Bromine → 2-(3-Acetylamino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester hydrobromide

HRID 1170513Notes

Reaction equation

HRID 1170513 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]([NH:18][C:19]([NH2:24])=[N:20][C:21](=[O:23])[CH3:22])=[S:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25]Br>C(O)C.C(Cl)(Cl)Cl>[BrH:25].[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[S:17][N:24]=[C:19]([NH:20][C:21](=[O:23])[CH3:22])[N:18]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 178475106HCID 178475106, compound

Product 1

HCID 686956592-(3-Acetylamino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester hydrobromideYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6212ChloroformSolvent

Procedure

2-(N′-Acetyl-guanidinocarbothioyl)-pyrrolidine-1-carboxylic acid benzyl ester (13.0 g, 37.4 mmol) was dissolved in ethanol (80 mL). The ethanol solution was cooled to 0° C. and a solution of bromine (6.50 g, 40.6 mmol) in chloroform (30 mL) was added dropwise over 5 minutes. The resulting solution was allowed to return to room temperature while stirring for 3 hours. The reaction mixture was concentrated under vacuo to afford 14.0 g (88%) of 2-(3-acetylamino-[1,2,4]thiadiazol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester hydrobromide.

Workup

  1. customto return to room temperature
  2. concentrationThe reaction mixture was concentrated under vacuo

Sources & evidence

ORD record
ord-62f2e5ba03ed4098a219afda6cfb7432
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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