Chlorotrimethylsilane → L-Aspartic acid, N-(trimethylsilyl)-, bis(phenylmethyl) ester

HRID 64797Notes

Reaction equation

HRID 64797 reaction equation
[NH2:1][C@H:2]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[CH3:24][Si:25]([CH3:28])([CH3:27])Cl.C(N(CC)CC)C>C(OCC)C>[CH3:24][Si:25]([CH3:28])([CH3:27])[NH:1][C@H:2]([C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 2808532Dibenzyl L-aspartate

Product 1

HCID 11373549L-Aspartic acid, N-(trimethylsilyl)-, bis(phenylmethyl) ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The dibenzyl (S)-aspartate in anhydrous diethyl ether (200 ml) is cooled in an ice-bath under a nitrogen atmosphere. Trimethylchlorosilane (12.7 ml, 0.1 mole) is added to the stirred solution to give a white precipitate. Triethylamine (14.0 ml, 0.1 mole) is then added to the mixture. The cooling bath is removed and the mixture is stirred at room temperature (22°-25° C.) for 2 hrs. The mixture is then filtered directly into a 3-neck, 1.0 liter, round bottom flask fitted with a sintered glass funnel, magnetic stirrer, and a vacuum-nitrogen inlet. This operation is carried out under a blanket of nitrogen, care being taken to exclude atmospheric moisture. The sintered glass funnel is replaced by a stopper and the ether is evaporated under vacuum with stirring to provide dibenzyl (S)-N-trimethylsilylaspartate (35.5 g, 0.092 mole) as a slightly hazy oil.

Workup

  1. customto give a white precipitate
  2. customThe cooling bath is removed
  3. filtrationThe mixture is then filtered directly into a 3-neck, 1.0 liter, round bottom flask
  4. customfitted with a sintered glass funnel, magnetic stirrer
  5. customthe ether is evaporated under vacuum
  6. stirringwith stirring

Sources & evidence

ORD record
ord-6adccca8e4474c54b864d13c061fc7af
Source dataset
uspto-grants-1986_09
Patent number
US04610820

Reaction notes

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