Cesium carbonate → 2-[(4-Iodo-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester

HRID 2179926

반응식

HRID 2179926 반응식
[CH3:1][O:2][C:3](=[O:27])[CH:4]([NH:12][S:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH3:24])=[C:18]([CH3:25])[C:17]=1[CH3:26])(=[O:15])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[I:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:27])[CH:4]([N:12]([CH2:33][C:32]1[CH:35]=[CH:36][C:29]([I:28])=[CH:30][CH:31]=1)[S:13]([C:16]1[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH3:24])=[C:18]([CH3:25])[C:17]=1[CH3:26])(=[O:15])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 9542584-Iodobenzyl bromideHCID 50165302-(4-Methoxy-2,3,6-trimethyl-benzenesulfonylamino)-3-phenyl-propionic acid methyl ester

생성물 1

HCID 865904232-[(4-Iodo-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester수율 90%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(4-Methoxy-2,3,6-trimethyl-benzenesulfonylamino)-3-phenyl-propionic acid methyl ester (50 mg, 0.129 mmol) in anhydrous DMF (1 mL), 4-iodobenzyl bromide (46 mg, 0.154 mmol) and cesium carbonate (50 mg, 0.154 mmol) were added and the reaction mixture was stirred at room temperature under a N2 atmosphere for 12 h. The reaction mixture was partitioned between water and ether. The ether layer was separated, dried (Na2SO4), concentrated. The residue was purified by silica gel column chromatography using ethyl acetate and hexane (1:3) as eluent to obtain 2-[(4-Iodo-benzyl)-(4-methoxy-2,3,6-trimethyl-benzenesulfonyl)-amino]-3-phenyl-propionic acid methyl ester (68 mg, 90%) as a foam. 1H NMR (CDCl3, 400 MHz): δ7.48 (d, 2H), 7.21 (m, 3H), 7.09 (d, 2H), 6.91(d, 2H), 6.45 (s, 1H), 4.60 (m, 3H), 3.81 (s, 3H), 3.38 (s, 3H), 3.17 (dd, 1H), 2.81 (dd, 1H), 2.63, 2.44, 2.14 (3s, 9H).

후처리

  1. customThe reaction mixture was partitioned between water and ether
  2. customThe ether layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-15104b34d46046b7ac7fa53963d4939f
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887877B2

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