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Sodium Iodide → 2-Methyl-2-[(1-phenethyloxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-propionic acid methyl ester

HRID 874744
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인쇄 미리보기

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HRID 874744 반응식
[CH3:1][O:2][C:3](=[O:21])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]=1[OH:20])=[O:9])([CH3:6])[CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[I-].[Na+]>CN(C)C=O.O.C(OCC)C>[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:6])([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:11]=1[O:20][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:9])[CH3:5]
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참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 7666Phenethyl bromideHCID 10796Cesium carbonateHCID 57912188HCID 57912188, 화합물

생성물 1

HCID 688447242-Methyl-2-[(1-phenethyloxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-propionic acid methyl ester수율 63.5%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 3283Diethyl Ether용매
HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

80 mg 2-[(1-hydroxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-2-methyl-pro-pionic acid methyl ester, 224 mg cesium carbonate, 61 mg of (2-bromoethyl)-benzene and 4 mg sodium iodide were dissolved in 5 ml of N,N-dimethylformamide and stirred at 80° C. for 6 h. 10 ml of diethyl ether and 10 ml of water were added to the reaction. The organic layer was separated and washed again with 10 ml of water. It was then dried over magnesium sulphate, filtered and concentrated in vacuo. Purification by flash chromatography (silica, heptanes/ethyl acetate) afforded 69 mg of 2-methyl-2-[(1-phenethyloxy-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-amino]-propionic acid methyl ester.

후처리

  1. customThe organic layer was separated
  2. washwashed again with 10 ml of water
  3. dry with materialIt was then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (silica, heptanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-c1ada699085743b69283b672e455f424
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08980938B2

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