Trifluoroacetic acid → HCID 54591107, compound

HRID 1619991Notes

Reaction equation

HRID 1619991 reaction equation
COC1C=CC(C[N:8]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][C:18]4[N:21]=[C:22]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[O:23][C:17]=4[CH2:16]3)[CH:12]3[CH:10]([CH2:11]3)[C:9]2=[O:30])=CC=1.C1(OC)C(=CC=CC=1)OC.C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>>[C:24]1([C:22]2[O:23][C:17]3[CH2:16][N:15]([C:13]4[CH:12]5[CH:10]([CH2:11]5)[C:9](=[O:30])[NH:8][N:14]=4)[CH2:20][CH2:19][C:18]=3[N:21]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7043VeratroleHCID 10340Sodium CarbonateHCID 67465135HCID 67465135, compound

Product 1

HCID 54591107HCID 54591107, compound

Procedure

320 mg (0.75 mmol) 3-(4-methoxy-benzyl)-5-(2-phenyl-6,7-dihydro-4H-oxazolo[5,4-c]pyridin-5-yl)-3,4-diaza-bicyclo[4.1.0]hept-4-en-2-one, 1 ml (7.84 mmol) Veratrol and 6 ml TFA are heated to 100° C. in a pressure vessel for 24 h. The cooled mixture is combined with sat. sodium carbonate solution and extracted with DCM, the org. phase is concentrated by rotary evaporation i. V. and the residue is purified by silica gel (eluant: DCM/methanol).

Workup

  1. extractionextracted with DCM
  2. concentrationphase is concentrated by rotary evaporation i
  3. customand the residue is purified by silica gel (eluant: DCM/methanol)

Sources & evidence

ORD record
ord-cee0d33ea51b49d0ae7a2435873ed509
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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