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Benzoyl chloride → O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-beta-benzoyloxytyrosine methyl ester

HRID 1587285
ノート
印刷プレビュー

反応式

HRID 1587285 の反応式
[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH:17]([OH:28])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][O:26][CH3:27])=[CH:20][CH:19]=1)[N:5]([CH3:16])[S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].C(N(CC)CC)C.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CN(C)CCCN>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH:17]([O:28][C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][O:26][CH3:27])=[CH:22][CH:23]=1)[N:5]([CH3:16])[S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 7412Benzoyl chlorideHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8471TriethylamineHCID 54118395O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-beta-hydroxytyrosine methyl ester

生成物 1

HCID 54000197O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-beta-benzoyloxytyrosine methyl ester収率 93.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6344Dichloromethane溶媒

実験手順

To a solution of O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-β-hydroxytyrosine methyl ester (erythro isomer) (3.85 g) in dichloromethane (30 ml) were added triethylamine (1.38 g), 4-dimethylaminopyridine (0.45 g) and benzoyl chloride (1.92 g). After stirring for 16 hours at room temperature, 3-dimethylaminopropylamine (3.3 g) was added to the mixture and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (30 ml) and washed with dil. hydrochloric acid, sodium bicarbonate aqueous solution and water. After evaporating, the residue was put on a column of silica gel (MERCK 7734, 150 g) and eluted with n-hexane-ethyl acetate (5:2, V/V) to give O-methoxymethyl-N-methyl-N-(2-nitrophenylthio)-β-benzoyloxytyrosine methyl ester (erythro isomer) (4.49 g).

後処理

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (30 ml)
  3. washwashed with dil. hydrochloric acid, sodium bicarbonate aqueous solution and water
  4. customAfter evaporating
  5. washeluted with n-hexane-ethyl acetate (5:2, V/V)

出典と根拠

ORDレコード
ord-2a2e8bddee7d4be2b1b36b3e0d88c4df
出典データセット
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05217952

反応ノート

読み込み中…

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