Propargyl bromide → 2-[(4-Methoxy-2,3,6-trimethyl-benzenesulfonyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid methyl ester

HRID 2179931

반응식

HRID 2179931 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.[CH2:28](Br)[C:29]#[CH:30].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:27])[CH:4]([N: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])[CH2:30][C:29]#[CH:28])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 50165302-(4-Methoxy-2,3,6-trimethyl-benzenesulfonylamino)-3-phenyl-propionic acid methyl ester

생성물 1

HCID 207793062-[(4-Methoxy-2,3,6-trimethyl-benzenesulfonyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid methyl ester수율 85%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A DMF (8 mL) solution of 2-(4-Methoxy-2,3,6-trimethyl-benzenesulfonylamino)-3-phenyl-propionic acid methyl ester (prepared according to example 2, step I) (200 mg) was cooled to 0° C. and then propargyl bromide (80%, 0.07 mL, 0.61 mmol) and Cs2CO3 (200 mg, 0.61 mmol) were added under an atmosphere of N2. The ice bath was removed and the reaction mixture was stirred at room temperature for 12 h. The mixture was partitioned between ether and water, the ether layer was separated, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using ethyl acetate and hexane (1:3) as eluent to obtain 2-[(4-Methoxy-2,3,6-trimethyl-benzenesulfonyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid methyl ester (185 mg, 85%) as a solid. 1H NMR (CDCl3, 400 MHz): δ7.20-7.17 (m, 3H), 7.10-7.08 (m, 2H), 6.56 (s, 1H), 4.42-4.29 (m, 3H), 3.86 (s, 3H), 3.56 (s, 3H), 3.32 (dd, 1H), 3.26 (dd, 1H), 2.66, 2.35 (2s, 6H), 2.21 (t, 1H), 2.08(s, 3H).

후처리

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

출처 및 근거

ORD 기록
ord-d9a879b7093a4e38bd7b0ef8b16f4125
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887877B2

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