Hydrochloric Acid → HCID 59401128, compound

HRID 77003Notes

Reaction equation

HRID 77003 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(O[C@@H:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([O:17][CH3:18])=[O:16])(=O)=O.Cl>C(#N)C>[CH3:18][O:17][C:15](=[O:16])[C@H:14]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7515N-MethylanilineHCID 10999262(S)-methyl 2-(methylsulfonyloxy)-2-phenylacetate

Product 1

HCID 59401128HCID 59401128, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

N-methylaniline (299 ul, 2.76 mmol) is added to a solution of (S)-methyl 2-(methylsulfonyloxy)-2-phenylacetate (I5) (450 mg, 1.84 mmol) in acetonitrile (10 mL). The reaction is heated at 120° C. for 15 minutes (microwave irradiation). 2N HCl (5 mL) is added and the mixture is extracted with EtOAc. The organic phase is dried over sodium sulphate and the solvent is evaporated to dryness. The crude is purified by flash chromatography on silica gel (Petroleum ether/Et2O=9/1) to obtain intermediate I121 as an orange amorphous solid (125 mg, 27% yield).

Workup

  1. custom(microwave irradiation)
  2. extractionthe mixture is extracted with EtOAc
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customthe solvent is evaporated to dryness
  5. customThe crude is purified by flash chromatography on silica gel (Petroleum ether/Et2O=9/1)

Sources & evidence

ORD record
ord-7b3048926ed14dbf8ced51132ac17894
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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