Ethyl Acetate → HCID 89813652, compound

HRID 525347Notes

Reaction equation

HRID 525347 reaction equation
[NH2:1][C@@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])[C:3]([OH:5])=[O:4].S(Cl)([Cl:15])=O.[CH3:17]COC(C)=O>CO.CCCCCC>[Cl-:15].[CH3:17][O:4][C:3](=[O:5])[C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])[NH3+:1]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 1501939HCID 1501939, compound

Product 1

HCID 89813652HCID 89813652, compoundYield 95.78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a suspension of (S)-2-amino-2-(o-tolyl)acetic acid (commercially available from ACES Pharma, Princeton, N.J.) (800 mg, 4.84 mmol) in MeOH (20 mL) was added thionyl chloride (633.77 mg, 5.32 mmol) dropwise at −10° C. The resulting reaction mixture was stirred for 12 hours at reflux. After completion of the reaction (Reaction monitored by TLC, TLC system: 50% EtOAc in hexane), the reaction mixture was cooled to ambient temperature and then concentrated under reduced pressure. The residue was crystallized with MeOH and diethyl ether to afford (S)-2-methoxy-2-oxo-1-(o-tolyl)ethanaminium chloride, (1 g, 95.78%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.97 (s, 3H), 7.39-7.28 (m, 4H), 5.34 (s, 1H), 3.70 (s, 3H), 2.43 (s, 3H). m/z (ESI) 180.1 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureat reflux
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was crystallized with MeOH and diethyl ether

Sources & evidence

ORD record
ord-30799f4d4efa456898b971d2fa976cb7
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

Loading…