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

HRID 582591

반응식

HRID 582591 반응식
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][S:3]1.Cl.[CH3:11][C@H:12]([NH2:18])[CH2:13][O:14][N+:15]([O-:17])=[O:16].C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[CH3:11][C@H:12]([NH:18][C:7]([C@@H:5]1[CH2:4][S:3][C:2](=[O:1])[NH:6]1)=[O:9])[CH2:13][O:14][N+:15]([O-:17])=[O:16]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 72390ProcysteineHCID 199401P,P-Diphenylphosphinic azideHCID 86754033(1S)-1-Methyl-2-nitroxyethylamine hydrochloride

생성물 1

HCID 9816362(4R)-N-[(1S)-1-Methyl-2-nitroxyethyl]-2-oxothiazolidin-4-yl-carboxamide수율 94.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In 60 ml of dry tetrahydrofuran were suspended 2.06 g of (4R)-2-oxothiazolidine-4-carboxylic acid and 2.00 g of (1S)-1-methyl-2-nitroxyethylamine hydrochloride, 4.5 ml of triethylamine and 3.00 ml of diphenylphosphoryl azide were added thereto with stirring under ice-cooling, and the mixture was stirred at room temperature for 5 hours. Then, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography employing cyclohexane-ethyl acetate (1:4) as an eluent to obtain 3.00 g of colorless crystals. The crystals were recrystallized from ethyl acetate to obtain 0.964 g of the desired compound as colorless needle crystals.

후처리

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

출처 및 근거

ORD 기록
ord-92c3c08958e34ac08653b24b825b3693
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05925658

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