3-(4-Hydroxyphenyl)propionic acid → 3-(4-Hydroxy-phenyl)-2-[3-(4-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester

HRID 546366

Reaction equation

HRID 546366 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15](=[O:26])[CH:16]([NH2:25])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:13][O:14][C:15](=[O:26])[CH:16]([NH:25][C:10](=[O:11])[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 10868DicyclohexylcarbodiimideHCID 76957DL-Methyl tyrosinate

Product 1

HCID 118576273-(4-Hydroxy-phenyl)-2-[3-(4-hydroxy-phenyl)-propionylamino]-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3(4-hydroxy phenyl) propionic acid (10 grams, 60.17 mmol) and Example 1 (11.7 grams, 60.00 mmol) in anhydrous dichloro methane (100 mL) under a nitrogen atmosphere at 0° C. is added dropwise to a solution of 1,3-dicyclohexyl carbodiimide(31 grams, 150.24 mmol) in dichloro methane (75 mL). The mixture is stirred at room temperature for 6 hours. The resulting solids are filtered off. The organic phase is washed with 5% sodium bicarbonate (2×25 mL) and water (2×25 mL), dried over sodium sulphate, and distilled to give crude 23, which can be purified in appropriate solvent.

Workup

  1. customat 0° C.
  2. filtrationThe resulting solids are filtered off
  3. washThe organic phase is washed with 5% sodium bicarbonate (2×25 mL) and water (2×25 mL)
  4. dry with materialdried over sodium sulphate
  5. distillationdistilled
  6. customto give crude 23, which
  7. customcan be purified in appropriate solvent

Sources & evidence

ORD record
ord-dba28217c61a4b0e8d72a8c4a731401a
Source dataset
uspto-grants-2011_05
Patent number
US07935843B2

Linked notes

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