Sulfuric Acid → N-carbobenzoxy-D-alanine(1-methyl-1-cyclopentyl)ester

HRID 35443

反応式

HRID 35443 の反応式
[C:1]([NH:11][C@@H:12]([C:14]([OH:16])=[O:15])[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(=O)(=O)(O)O.[CH3:22][C:23]1[CH2:27][CH2:26][CH2:25][CH:24]=1>ClCCl>[CH3:22][C:23]1([O:15][C:14](=[O:16])[C@@H:12]([CH3:13])[NH:11][C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])[CH2:27][CH2:26][CH2:25][CH2:24]1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 127461-MethylcyclopenteneHCID 70832N-Cbz-d-alanine

生成物 1

HCID 22839475N-carbobenzoxy-D-alanine(1-methyl-1-cyclopentyl)ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a magnetically stirred solution of 22.3 g (0.1 mol) N-Cbz-D-alanine in 50 mls of dry dichloromethane containing 0.5 mls of concentrated sulfuric acid at 0° C., was added dropwise a 10 g (0.1 mol) sample of 1-methylcyclopentene in 50 mls of dichloromethane. After 5 days of stirring at room temperature, the mixture was heated to reflux for 4 hours, after which the reaction was cooled to room temperature, washed with 100 mls of saturated NaHCO3, 100 mls of water and dried over MgSO4. Filtration followed by evaporation of the solvent yielded 1.81 g of the product. NMR(CDCl3): δ1.3-1.4(d, 3H), 1.5(s, 3H), 1.5-1.7 (m, 8H), 4.2 (m, 1H), 5.05 (s, 2H), 5.25 (m, 1H), 7.3 (s, 5H).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureafter which the reaction was cooled to room temperature
  4. washwashed with 100 mls of saturated NaHCO3, 100 mls of water
  5. dry with materialdried over MgSO4
  6. filtrationFiltration
  7. customfollowed by evaporation of the solvent

出典と根拠

ORDレコード
ord-7c5d170a29c34f9494571d4c21b41012
出典データセット
uspto-grants-1988_08
特許番号
US04766246

関連ノート

読み込み中…