Methanol → (R)-Methyl 2-amino-3-(naphthalen-2-yl)propanoate

HRID 1701024Notes

Reaction equation

HRID 1701024 reaction equation
S(Cl)(Cl)=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[CH2:15][C@H:16]([C:18]([OH:20])=[O:19])[NH2:17].[CH3:21]O>>[CH3:21][O:19][C:18](=[O:20])[C@@H:16]([CH2:15][C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=1)[NH2:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2733661D-3-(2-Naphthyl)alanine

Product 1

HCID 7016520(R)-Methyl 2-amino-3-(naphthalen-2-yl)propanoate

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (5 ml) was added dropwise over 15 min. to a suspension of (R)-3-(2-naphthyl)alanine (5.0 g) in methanol (50 ml) at 35° C. After addition the mixture was heated at 60° C. for 1 h, cooled and the solvent removed in vacuo. Water (75 ml) and ethyl acetate (125 ml) were added and pH was adjusted to 8.5 with sodium carbonate. The organic phase was separated and dried (magnesium sulfate) to afford 4.86 g of (R)-3-(2-naphthyl)alanine methyl ester.

Workup

  1. additionAfter addition the mixture
  2. temperaturecooled
  3. customthe solvent removed in vacuo
  4. additionWater (75 ml) and ethyl acetate (125 ml) were added
  5. customThe organic phase was separated
  6. dry with materialdried (magnesium sulfate)

Sources & evidence

ORD record
ord-84eb9e3bf8a5469d9bd6840d98f1248b
Source dataset
uspto-grants-2002_02
Patent number
US06350767B1

Reaction notes

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