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

HRID 849833Notes

Reaction equation

HRID 849833 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-9fee042f5a194b0a99ca3fec5acf6ec1
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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