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

HRID 442758

反応式

HRID 442758 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-91ff4ee8f9bc4b65ad9810482c255100
出典データセット
uspto-grants-1999_04
特許番号
US05891898

関連ノート

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