Diethyl Ether → Dibenzyl L-aspartate

HRID 64812Notes

Reaction equation

HRID 64812 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@H:13]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C(OCC)C.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:12][C@H:13]([C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 2808531L-Aspartic acid, 1,4-bis(phenylmethyl) ester, 4-methylbenzenesulfonate (1:1)

Product 1

HCID 2808532Dibenzyl L-aspartateYield 100.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of dibenzyl (S)-aspartate p-toluenesulfonic acid salt (48.6 g, 0.1 mole), diethylether (300 ml), water (100 ml), and saturated aqueous potassium carbonate (50 ml) is shaken vigorously. The layers are separated and the aqueous portion is extracted with more ether (2×100 ml). The combined ethereal extracts are washed with brine, dried with magnesium sulfate, filtered, and evaporated under vacuum to afford dibenzyl (S)-aspartate (31.5 g) as a water white liquid.

Workup

  1. customThe layers are separated
  2. extractionthe aqueous portion is extracted with more ether (2×100 ml)
  3. washThe combined ethereal extracts are washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-918427aefe5c4580a4d3968245c45081
Source dataset
uspto-grants-1986_09
Patent number
US04610820

Reaction notes

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