Hydrochloric Acid → HCID 178513090, compound

HRID 733261Notes

Reaction equation

HRID 733261 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH2+:4].CC([O-])(C)C.[K+].C([O:14][C:15](=O)[CH2:16][CH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:24]=2)[C:19](=[O:30])[N:18]1[CH2:31][C:32]([F:35])([F:34])[F:33])C.Cl>O>[O:30]=[C:19]1[C:20]2[C:25](=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=2)[CH:17]([CH2:16][C:15]([NH:4][C:3]([NH2:5])=[NH:2])=[O:14])[N:18]1[CH2:31][C:32]([F:34])([F:33])[F:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 57678949ethyl (RS)-[3-oxo-2-(2,2,2-trifluoroethyl)-6-trifluoromethyl-2,3-dihydro-1H-isoindol-1-yl]acetateHCID 131726207Guanidinium hydrochloride

Product 1

HCID 178513090HCID 178513090, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.24 g guanidinium hydrochloride and 1.21 g of KOtBu were suspended using 30 ml of DMF(anhydrous) and stirred for 30 minutes at ambient temperature. Then, a solution of 0.8 g of [3-oxo-2-(2,2,2-trifluoro-ethyl)-6-trifluoromethyl-2,3-dihydro-1H-isoindol-1-yl]-acetic acid ethyl ester in 5 ml of DMF(anhydrous) were added and the mixture was stirred for 17 h at ambient temperature. The mixture was then poured into 100 ml of water and the pH was adjusted to pH=8 using aqueous HCl-solution. The aqueous layer was extracted three times using 100 ml of EA each. The organic layer was dried over MgSO4 and the solvent was removed in vacuo. Chromatography on silica gel using EA/MeOH 3:1 yielded 0.56 g of an amorphous solid (Rf(EA/MeOH 3:1)=0.45, MS (ES+): 383 (M+1)+).

Workup

  1. stirringthe mixture was stirred for 17 h at ambient temperature
  2. extractionThe aqueous layer was extracted three times
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7f2695f659a240f2919f1b93247215dd
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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