Dicyclohexylcarbodiimide → 3-(4-Hydroxy-phenyl)-2-(2-{2-[3-(4-hydroxy-phenyl)-propionyloxy]-acetoxy}-acetylamino)-propionic acid methyl ester

HRID 2090577Notes

Reaction equation

HRID 2090577 reaction equation
[C:1]([CH2:4][O:5][C:6](=[O:16])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([OH:3])=[O:2].[CH3:17][O:18][C:19](=[O:34])[CH:20]([NH:29][C:30](=[O:33])[CH2:31]O)[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:17][O:18][C:19](=[O:34])[CH:20]([NH:29][C:30](=[O:33])[CH2:31][O:2][C:1](=[O:3])[CH2:4][O:5][C:6](=[O:16])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 584275083-(4-Hydroxy-phenyl)-propionic acid carboxymethyl esterHCID 588958052-(2-Hydroxy-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester

Product 1

HCID 584275123-(4-Hydroxy-phenyl)-2-(2-{2-[3-(4-hydroxy-phenyl)-propionyloxy]-acetoxy}-acetylamino)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(4-hydroxy-phenyl)-propionic acid carboxymethyl ester 5 (10 grams, 44.64 mmol) and 2-(2-hydroxy-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester 3 (11.3 grams, 44.66 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 (23 grams, 111.47 mmol) in dichloro methane (60 mL). 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 8, which can be purified in an appropriate solvent.

Workup

  1. filtrationThe resulting solids are filtered off
  2. washThe organic phase is washed with 5% sodium bicarbonate (2×25 mL) and water (2×25 mL)
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled
  5. customto give crude 8, which
  6. customcan be purified in an appropriate solvent

Sources & evidence

ORD record
ord-37d5d44ee1894fb2aaf296bd6a7f68c5
Source dataset
uspto-grants-2013_05
Patent number
US08436201B2

Reaction notes

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