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

HRID 442758

반응식

HRID 442758 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-91ff4ee8f9bc4b65ad9810482c255100
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891898

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