Sodium Carbonate → Methyl (3r)-3-amino-4-(2,4,5-trifluorophenyl)butanoate

HRID 84153Notes

Reaction equation

HRID 84153 reaction equation
C(O)(=O)[C@@H](C1C=CC=CC=1)O.[NH2:12][C@H:13]([CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:14][C:15]([O:17][CH3:18])=[O:16].C([O-])([O-])=O.[Na+].[Na+]>O>[NH2:12][C@H:13]([CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 49784071(R)-Methyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate (R)-2-hydroxy-2-phenylacetate

Product 1

HCID 49784072Methyl (3r)-3-amino-4-(2,4,5-trifluorophenyl)butanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The methyl(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoate (R)-(−)-mandelate (30) (113.0 gm) was taken in water (10.0 vol, 1.13 Ltr) and the suspension was stirred for 10-15 minutes. The suspension was further basified by using a 10% Na2CO3 solution (1.0 vol, 113.0 ml) until the pH of the reaction mixture reached 8-9. The product was extracted in ethyl acetate (2×10.0 vol, 2×1.13 Ltr). The combined ethyl acetate layers were further washed with water (2×10.0 vol, 2×1.13 Ltr). The product was isolated as a pale yellow oil by complete distillation of the ethyl acetate under reduced pressure at 45-50° C.

Workup

  1. extractionThe product was extracted in ethyl acetate (2×10.0 vol, 2×1.13 Ltr)
  2. washThe combined ethyl acetate layers were further washed with water (2×10.0 vol, 2×1.13 Ltr)
  3. customThe product was isolated as a pale yellow oil by complete distillation of the ethyl acetate under reduced pressure at 45-50° C.

Sources & evidence

ORD record
ord-18a0feadea884bd19086f20bbbf82cc9
Source dataset
uspto-grants-2014_09
Patent number
US08846916B2

Reaction notes

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