Methanol → HCID 66807983, compound

HRID 1182409Notes

Reaction equation

HRID 1182409 reaction equation
S(Cl)([Cl:3])=O.[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[NH:15][CH2:16][C:17]([OH:19])=[O:18].[CH3:20]O>>[ClH:3].[CH3:20][O:18][C:17](=[O:19])[CH2:16][NH:15][C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 457448Glycine, N-2-naphthalenyl-

Product 1

HCID 66807983HCID 66807983, compoundYield 94%

Procedure

33 mL of thionyl chloride was added dropwise to a mixture of 50.3 g of 2-naphthylglycine (racemic body) and 200 mL of methanol (dehydrated) at an inner temperature of 35° C. inner temperature over 1 hour and the mixture was stirred at the same temperature for 3 hours to effect reaction. The reaction mixture was concentrated and the resulting concentrated residue was mixed with 200 mL of diethyl ether. Then, the crystals produced were recovered by filtration and washed with 50 mL of diethyl ether. The crystals recovered by filtration were dried at an inner temperature of 50° C. under reduced pressure to obtain 59.0 g of white 2-naphthylglycine methyl ester hydrochloride (yield: 94%).

Workup

  1. customreaction
  2. concentrationThe reaction mixture was concentrated
  3. additionthe resulting concentrated residue was mixed with 200 mL of diethyl ether
  4. customThen, the crystals produced
  5. filtrationwere recovered by filtration
  6. washwashed with 50 mL of diethyl ether
  7. filtrationThe crystals recovered by filtration
  8. customwere dried at an inner temperature of 50° C. under reduced pressure

Sources & evidence

ORD record
ord-e00e61aaf4ab4ce4a2e258996bdcc01a
Source dataset
uspto-grants-2007_10
Patent number
US07288674B2

Reaction notes

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