Triethylamine → 2-(2-Benzyloxy carbonyl methoxy-acetyl amino)-3-(4-hydroxy-phenyl)-propionic acid ethyl ester

HRID 1257295노트

반응식

HRID 1257295 반응식
[CH2:1]([O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[NH2:6])[CH3:2].C(N(CC)CC)C.[CH2:23]([O:30][C:31](=[O:38])[CH:32]([C:35](Cl)=[O:36])OC)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:39](OCC)(=[O:41])C>>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([N:6]([O:41][CH3:39])[C:35](=[O:36])[CH2:32][C:31]([O:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:38])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[CH3:2]

참가 물질

5

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 70364L-Tyrosine ethyl esterHCID 86669389Chlorocarbonyl methoxy-acetic acid benzyl ester

생성물 1

HCID 866693902-(2-Benzyloxy carbonyl methoxy-acetyl amino)-3-(4-hydroxy-phenyl)-propionic acid ethyl ester

실험 절차

To a mixture of Tyrosine ethyl ester (40 g) and Triethylamine (40 ml) in Ethyl acetate (600 ml) at 0° C. temperature was added Chloro carbonyl methoxy-acetic acid benzyl ester (46.5 g) drop wise. The reaction mixture was further stirred at room temperature for 10 hours. The solids were filtered off and the organic phase was washed with 5% sodium bicarbonate solution (600 ml) and water (600 ml). It was dried over sodium sulphate and organic solvent was distilled. The crude was purified by column chromatography on silica gel using Hexane:Ethyl acetate (8:2) to get pure 2-(2-Benzyloxy carbonyl methoxy-acetyl amino)-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (30 g) as a light yellow syrup. The product was characterized by 1H NMR (CDCl3) δ 1.20 (t, 3H, CH3), 2.90 to 3.10 (m, 2H, CH2), 4.10 to 4.30 (m, 6H, 3X CH2), 4.85 (q, 1H, CH), 5.20 (s, 2H, CH2), 5.80 (bs, 1H, NH), 6.70 (d, 2H, Ar), 7.00 (d, 2H, Ar), 7.40 (m, 5H, Ar).

후처리

  1. filtrationThe solids were filtered off
  2. washthe organic phase was washed with 5% sodium bicarbonate solution (600 ml) and water (600 ml)
  3. dry with materialIt was dried over sodium sulphate and organic solvent
  4. distillationwas distilled
  5. customThe crude was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-4c5cdd682cad4674afde3551c2668b2a
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461372B2

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