Pyridine → N-methoxycarbonyl-L-tyrosine benzyl ester

HRID 274087ノート

反応式

HRID 274087 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:31])[C@H:21]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1.ClCCl.Cl[C:42]([O:44][CH3:45])=[O:43]>O>[CH2:12]([O:19][C:20](=[O:31])[C@H:21]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=1)[NH:22][C:42]([O:44][CH3:45])=[O:43])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 104540O-benzyl-L-tyrosine toluene-p-sulphonate

生成物 1

HCID 54118506N-methoxycarbonyl-L-tyrosine benzyl ester

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To an ice-cooled mixture of L-tyrosine benzyl ester p-toluenesulfonate (41.0 g), pyridine (16.4 ml), and dichloromethane (92 ml) was added methyl chloroformate (7.8 ml). The mixture was stirred in an ice-bath for 1 hour, diluted with water, and extracted once with dichloromethane. The extract was concentrated in vacuo and the residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Purification of the crude product by column chromatography on silica gel (gradient elution; 10:1 to 5:1 chloroform-ethyl acetate) gave N-methoxycarbonyl-L-tyrosine benzyl ester (22.0 g).

後処理

  1. extractionextracted once with dichloromethane
  2. concentrationThe extract was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude product by column chromatography on silica gel (gradient elution; 10:1 to 5:1 chloroform-ethyl acetate)

出典と根拠

ORDレコード
ord-a8b25bcf9a0b44ff970acb08cc2a1871
出典データセット
uspto-grants-1995_02
特許番号
US05387710

反応ノート

読み込み中…