Methyl iodide → HCID 86602358, 화합물

HRID 2111869노트

반응식

HRID 2111869 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:29]([O-])(O)=O.[Na+].IC.C(Cl)(Cl)Cl.CO>CN(C=O)C.O.C(OCC)(=O)C>[CH3:29][O:11][C:10](=[O:12])[C@@H: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]([O:20][C:21]2[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1

참가 물질

8

반응물 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 21584188Chloroform methanolHCID 59751099N-(tert-Butoxycarbonyl)-O-(4-formylphenyl)-L-tyrosine

생성물 1

HCID 86602358HCID 86602358, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Dissolve (S)-2-tert-butoxycarbonylamino-3-(4-(4-formylphenoxy)phenyl)-propanoic acid (2.97 Kg, 7.7 moles) in dry DMF (14.84 L). Add NaHCO3 (1.29 Kg, 15.4 moles) and iodomethane (6.56 Kg, 46.19 moles) under inert atmosphere and stirred at room temperature for 14 h. Check completion of the reaction by TLC (SiO2 gel, CHCl3-MeOH, 9:1). Poured the reaction mixture in water and stirred for 15 min. Add ethyl acetate (40 L). Oraganic layer was washed with brine and evaporated under reduced pressure. Yield 3.06 Kg, 99.3%, HPLC purity 94.6% and chiral purity 100% ee. 1HNMR (300 MHz, CDCl3): 9.92 (s, 1H), 7.83 (d, J=8.7 Hz, 2H), 7.16 (d, J=8.7 Hz, 2H), 7.02 (overlapped d, 4H), 5.03 (brs, 1H), 4.59 (m, 1H), 3.74 (s, 3H), 3.13 (dd, J=5.7 and 13.8 Hz, 1H), 3.00 (dd, J=6.3 and 13.8 Hz, 1H), 1.43 (3, 9H).

후처리

  1. washOraganic layer was washed with brine
  2. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-97c36ddce1e04680b1afc1132dcdf0bc
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521465B2

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