Hydrochloric Acid → HCID 59424441, compound

HRID 1261316Notes

Reaction equation

HRID 1261316 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][NH:9][C:5]=2[C:4]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=2[F:18])=[N:3][CH:2]=1.[CH:19]1[CH:24]=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:20]=1.CCOC(/N=N/C(OCC)=O)=O.C(O)(C)C.Cl>C1COCC1.CO.C(Cl)Cl.CCOC(C)=O.CCCCCC>[F:18][C:12]1[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:11]=1[O:10][C:4]1[C:5]2[N:9]([CH:19]([CH3:24])[CH3:20])[CH:8]=[CH:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 59424466HCID 59424466, compound

Product 1

HCID 59424441HCID 59424441, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a suspension of 247 (80 mg, 0.327 mmol) in THF (4 mL), was added PPh3 (258 mg, 0.983 mmol), DEAD (0.155 mL, 0.983 mmol) and isopropanol (0.075 mL, 0.983 mmol), and the reaction mixture was allowed to stir for 48 hours. 3N HCl solution (1.0 mL) was added and the mixture was extracted with DCM. Aqueous phase was collected, neutralized with NaOH 10% (pH˜11) and extracted with DCM. The organic phase was collected, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified twice by column chromatography: eluents EtOAc/hexane (3:7) and MeOH/DCM (1:20), to afford title compound 248 (19 mg, 31% yield) as yellow solid. MS (m/z): 287.1 (M+1).

Workup

  1. extractionthe mixture was extracted with DCM
  2. customAqueous phase was collected
  3. extractionextracted with DCM
  4. customThe organic phase was collected
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified twice by column chromatography

Sources & evidence

ORD record
ord-2fc351ab4e0748f1801d47cedf9a919d
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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