Methyl iodide → (+-)-(R/S)-2-tert-Butoxycarbonylamino-3-(4-iodo-phenyl)-propionic acid methyl ester

HRID 900373노트

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HRID 900373 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH3:21][O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3409757Boc-p-iodo-DL-Phe-OH

생성물 1

HCID 13875796(+-)-(R/S)-2-tert-Butoxycarbonylamino-3-(4-iodo-phenyl)-propionic acid methyl ester수율 110.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

A solution of 2-tert-butoxycarbonylamino-3-(4-iodophenyl)-propanoic acid (5.0 g, 12.8 mmol) in DMF (50 mL) was treated with K2CO3 (2.2 g, 15.4 mmol). After stirring for 15 min, the solution was cooled to 0° C. and treated with iodomethane (1.0 mL, 15.4 mmol). After the addition was complete, the reaction mixture was stirred at room temperature for another 16 h, filtered and the resulting solid was washed with ethyl acetate (200 mL). The filtrate was washed successively with 5% aq HCl, sat. aq NaCl, dried over MgSO4 and concented. Purification by flash column chromatography (5% ethyl acetate in heptane) provided the desired product (5.74 g, 98%) as an oil. 1H NMR (CDCl3), δ 7.61 (d, J=9 Hz, 2 H), 7.74 (d, J=9, 2 H), 4.97 (d, J=7 Hz, 1 H), 4.56 (m, 1 H), 3.73 (s, 3 H), 3.02 (ddd, J=7, 7, 12 Hz, 2 H), 1.47 (s, 9H).

후처리

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred at room temperature for another 16 h
  3. filtrationfiltered
  4. washthe resulting solid was washed with ethyl acetate (200 mL)
  5. washThe filtrate was washed successively with 5% aq HCl, sat. aq NaCl
  6. dry with materialdried over MgSO4
  7. customPurification by flash column chromatography (5% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-b518d87cd94e468e84bf314dfa45bc3e
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358248B2

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