Triethylamine → HCID 54042817, compound

HRID 413616Notes

Reaction equation

HRID 413616 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.[CH3:17][Si:18]([CH3:33])([CH3:32])[CH2:19][CH2:20][O:21][C:22](=O)[O:23]N1C(=O)CCC1=O>ClCCl>[CH3:2][O:3][C:4](=[O:9])[CH:5]([NH:6][C:22]([O:21][CH2:20][CH2:19][Si:18]([CH3:33])([CH3:32])[CH3:17])=[O:23])[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate

Product 1

HCID 54042817HCID 54042817, compoundYield 108.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1.25 g serine methyl ester hydrochloride, 2.25 ml triethylamine and 10 ml dichloromethane was added at 0° C. a solution of 2.22 g carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-trimethylsilanyl-ethyl ester [R. E. Shute, D. H. Rich, Synthesis, 1987, 346]. After stirring for 24 h at rt the reaction mixture was washed two times with 1N potassium hydrogen sulfate, once with saturated sodium bicarbonate solution and once with brine. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 2.29 g of a colorless liquid.

Workup

  1. washwas washed two times with 1N potassium hydrogen sulfate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-32f4397a1e38411d81b70366178231fa
Source dataset
uspto-grants-2003_05
Patent number
US06569411B2

Reaction notes

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