Sodium Iodide → Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(4-chloro-2-nitrobenzyl)amino]propionate

HRID 1264592노트

반응식

HRID 1264592 반응식
[OH:1][CH2:2][CH:3]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[I-].[Na+].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[C:27]([N+:33]([O-:35])=[O:34])[CH:26]=1>CN(C)C=O>[OH:1][CH2:2][CH:3]([N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[CH2:29][C:28]1[CH:31]=[CH:32][C:25]([Cl:24])=[CH:26][C:27]=1[N+:33]([O-:35])=[O:34])[C:4]([O:6][CH3:7])=[O:5]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 5983994-Chloro-1-(chloromethyl)-2-nitrobenzeneHCID 11173760Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate

생성물 1

HCID 18612795Methyl 3-Hydroxy-2-[(4-methoxybenzenesulfonyl)-(4-chloro-2-nitrobenzyl)amino]propionate수율 115.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 0.289 g (1 mmol) of methyl 3-hydroxy-2-(4-methoxy-benzenesulfonylamino)propionate in 4 ml of N N-dimethylformamide cooled in an ice bath was added 40 mg of NaH (60% in oil) (1 mmol). After the gas evolution ceased, 0.165 g (1.1 mmol) of sodium iodide was added, followed by the addition of 0.226 g (1.1 mmol) of 4-chloro-2-nitrobenzyl chloride in 1 ml of dimethylformamide. The solution became purple and was stirred at room temperature over the weekend. The solvent was removed under vacuum and the residue extracted with CH2Cl2. The extract was washed with H2O, brine and dried with Na2SO4. The solvent was removed to give 0.53 g of solid which was chromatographed on thick layer silica gel plates with hexane-ethyl acetate (2:1) as solvent to give 0.143 g (31%) of product, as crystals, m.p. 112°-114° C. Anal. for C18H19ClN2O8S: Calc'd: C, 47.2; H, 4.2; N, 6.1; Found: C, 47.0; H, 4.1; N, 6.0.

후처리

  1. customThe solvent was removed under vacuum
  2. extractionthe residue extracted with CH2Cl2
  3. washThe extract was washed with H2O, brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed

출처 및 근거

ORD 기록
ord-3715a3bfed4d4deebfd9b58dae812b57
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06544984B1

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