Trifluoroacetic acid → HCID 66608477, compound

HRID 1529552Notes

Reaction equation

HRID 1529552 reaction equation
FC(F)(F)C(O)=O.CC(OC([N:15]1[CH2:22][C:21]2[O:20][C:19]([CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:18][C:17]=2[CH2:16]1)=O)(C)C>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[O:24]([CH2:23][C:19]1[O:20][C:21]2[CH2:22][NH:15][CH2:16][C:17]=2[N:18]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66608882HCID 66608882, compound

Product 1

HCID 66608477HCID 66608477, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

Trifluoroacetic acid (0.5 mL, 0.65 mmol) was added to a solution of 4,6-dihydro-2-(phenoxymethyl)-5H-pyrrolo[3,4-d]oxazole-5-carboxylic acid 1,1-dimethylethyl ester (0.075 g, 0.19 mmol) in DCM (0.5 mL). The mixture was stirred at room temperature for 15 minutes and diluted with a saturated solution of Na2CO3. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 5,6-dihydro-2-(phenoxymethyl)-4H-pyrrolo[3,4-d]oxazole (22 mg, 53% yield, 30% pure) as a clear oil that was used in the next step without further purification. C12H12N2O2LCMS: Rt 1.04, m/z 217 [M+H]+ (using method, LC-MS Method 6).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-7c4b1005e3104ea7bdd41103fa695b84
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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