Acetonitrile → (R)-3-(2-(acetoxymethyl)-4-amino-5-chloro-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

HRID 2378905Notes

Reaction equation

HRID 2378905 reaction equation
[C:1]([O:9][C@H:10]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([CH3:23])[C:17]=1[CH2:24][O:25][C:26](=[O:28])[CH3:27])[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C.[Cl:32]N1C(=O)CCC1=O>>[C:1]([O:9][C@H:10]([CH2:15][C:16]1[CH:21]=[C:20]([Cl:32])[C:19]([NH2:22])=[C:18]([CH3:23])[C:17]=1[CH2:24][O:25][C:26](=[O:28])[CH3:27])[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 31398ChlorosuccinimideHCID 59732065(R)-3-(2-(acetoxymethyl)-4-amino-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate

Product 1

HCID 59732080(R)-3-(2-(acetoxymethyl)-4-amino-5-chloro-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoateYield 57%

Procedure

(R)-3-(2-(acetoxymethyl)-4-amino-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate (15.00 g, 38.9 mmol) in acetonitrile (200. ml, 3829 mmol) was added N-chlorosuccinimide (5.72 g, 42.8 mmol). The reaction mixture was then heated to reflux for 2 min. The solvent was removed and the crude product was washed with aqueous NaHCO3. The crude product was purified by flash chromatography using 30% EtOAc in hexane to give (R)-3-(2-(acetoxymethyl)-4-amino-5-chloro-3-methylphenyl)-1-methoxy-1-oxopropan-2-yl benzoate in 57% yield. MS (ESI) 442 (M+H); Rf=2.42.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 2 min
  3. customThe solvent was removed
  4. washthe crude product was washed with aqueous NaHCO3
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-878b2e675cf54e4fb69ab426153a1013
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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