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

HRID 1648177
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HRID 1648177 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0594f55cf1a249a4a7d7bfa24202f90b
출처 데이터셋
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05436140

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