Sodium Carbonate → HCID 58286598, compound

HRID 2098460Notes

Reaction equation

HRID 2098460 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]2[C:19]([C@@H:21]([NH:26]C(=O)OC(C)(C)C)[C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:11].C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[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]2[C:19](=[O:20])[C@@H:21]([NH2:26])[C:22]([CH3:23])([CH3:24])[CH3:25])=[O:11]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 70234737HCID 70234737, compound

Product 1

HCID 58286598HCID 58286598, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 1,1-Dimethylethyl ((1S)-1-{[(1S,4S)-5-(1H-benzimidazol-2-ylcarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}-2,2-dimethylpropyl)carbamate (5.8 g, 12.7 mmol) in 60 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 (3×50 mL). The DCM solution was dried over anhydrous Na2SO4 and concentrated to give the title compound (3.6 g) as a pale yellow solid. LCMS (m/z): 356.2 (M+H).

Workup

  1. extractionextracted with DCM (3×50 mL)
  2. dry with materialThe DCM solution was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6039a4271a6b41e7a5998f0b07d1fbe1
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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