Sodium Carbonate → HCID 58286559, compound

HRID 2098458Notes

Reaction equation

HRID 2098458 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:17][C@@H:16]2[CH2:18][C@H:13]1[CH2:14][N:15]2C(OC(C)(C)C)=O)=[O:11].C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C@H:13]12[CH2:18][C@H:16]([NH:15][CH2:14]1)[CH2:17][N:12]2[C:10]([C:2]1[NH:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)=[O:11]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 58286517HCID 58286517, compound

Product 1

HCID 58286559HCID 58286559, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 1,1-Dimethylethyl (1S,4S)-5-(1H-benzimidazol-2-ylcarbonyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (20 g, 58.5 mmol) in 200 ml TFA/DCM (20%) was stirred at room temperature for 1 h. The reaction mixture was basified by addition of sat. aqueous Na2CO3 and then extracted with DCM (4×200 mL). The DCM solution was dried over anhydrous Na2SO4 and concentrated to give the title compound (6.5 g) as a pale yellow solid. LCMS (m/z): 243.1 (M+H).

Workup

  1. extractionextracted with DCM (4×200 mL)
  2. dry with materialThe DCM solution was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bfbd40965a5d440e9b0834a61a07f594
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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