Methyl iodide → HCID 86602358、化合物

HRID 2111869ノート

反応式

HRID 2111869 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 86602358HCID 86602358、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-97c36ddce1e04680b1afc1132dcdf0bc
出典データセット
uspto-grants-2009_04
特許番号
US07521465B2

反応ノート

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