Triethylamine → (4R)-N-[(1S)-1-Methyl-2-hydroxyethyl]-2-oxothiazolidin-4-yl-carboxamide

HRID 582592Notes

Reaction equation

HRID 582592 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][S:3]1.[NH2:10][C@H:11]([CH2:13][OH:14])[CH3:12].C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[CH3:12][C@H:11]([NH:10][C:7]([C@@H:5]1[CH2:4][S:3][C:2](=[O:1])[NH:6]1)=[O:9])[CH2:13][OH:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 72390ProcysteineHCID 80307L-AlaninolHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 21309140(4R)-N-[(1S)-1-Methyl-2-hydroxyethyl]-2-oxothiazolidin-4-yl-carboxamideYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 20 ml of dry tetrahydrofuran were dissolved 1.0 g of (4R)-2-oxothiazolidine-4-carboxylic acid and 0.56 g of L-alaninol, 2.8 ml of triethylamine and 1.8 ml of diphenylphosphoryl azide were added thereto with stirring under ice-cooling, and the mixture was stirred at room temperature for 3 hours. Then, the solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography employing ethyl acetate as an eluent and further purified by silica gel column chromatography employing dichloromethane-methanol (95:5) as an eluent to obtain 0.92 g of the desired compound as colorless crystals.

Workup

  1. additionwere added
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 3 hours
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography
  6. customfurther purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fc84290be5824f30835207a58956d429
Source dataset
uspto-grants-1999_07
Patent number
US05925658

Reaction notes

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