Methyl iodide → N-Methyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

HRID 1275784노트

반응식

HRID 1275784 반응식
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:6][O:7][C:8]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH2:5].[C:28](=O)([O-])[O-].[K+].[K+].IC>C(#N)C.ClCCl>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:6][O:7][C:8]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C:15]2[C:20]1=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:5][CH3:28]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15516030O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester

생성물 1

HCID 53855539N-Methyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester수율 4.6%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a mixture of 0.8 g (2.2 mmol) of O-(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester (Example 4a, Step 2) and 1.2 g (8.9 mmol) of potassium carbonate in acetonitrile (5 mL) was added 0.17 mL (2.7 mmol) iodomethane and the mixture stirred at room temperature for 16 h. The mixture was dissolved in dichloromethane, filtered and after evaporation of the solvent the residue was chromatographed on silica gel with 60% ethyl acetate in hexanes to give 0.038 g (yield 4.5%) N-Methyl--O--(9-phenyl-9H-fluoren-9-yl)-L-serine methyl ester as an oil. 1H NMR (CDCl3, 300 MHz) δ: 7.67 (d, 2H), 7.45-7.10 (m, 11H), 3.73 (s, 3 H), 3.35-3.15 (m, 3H), 2.37 (s, 3H), 2.06 (s, 1H); 13C NMR (CDCl3, 75 MHz) 6: 173.2, 146.6, 146.4, 143.1, 140.6, 129.2, 129.1, 128.3, 128.1, 128.0, 127.1, 125.4, 125.3, 125.1, 119.9, 88.3, 63.8, 62.9, 51.7.

후처리

  1. filtrationfiltered
  2. customafter evaporation of the solvent the residue
  3. customwas chromatographed on silica gel with 60% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-468d79d57ed541469845715aaf4c5165
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162824

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