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

HRID 1398107Notes

Reaction equation

HRID 1398107 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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, 3×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).

Workup

  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

Sources & evidence

ORD record
ord-65834894477747178e143b646f02b241
Source dataset
uspto-grants-2014_12
Patent number
US08901341B2

Reaction notes

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