Dicyclohexylcarbodiimide → 4-Hydroxy-benzoic acid [2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethyl carbamoyl]-methoxycarbonylmethyl ester

HRID 2090581Notes

Reaction equation

HRID 2090581 reaction equation
[C:1]([CH2:4][O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([OH:3])=[O:2].[CH3:15][O:16][C:17](=[O:32])[CH:18]([NH:27][C:28](=[O:31])CO)[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.[CH:33]1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH:18]([NH:27][C:28]([CH:4]([O:5][C:6](=[O:14])[C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[C:1]([O:3][CH3:33])=[O:2])=[O:31])[C:17]([O:16][CH3:15])=[O:32])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 58427513Benzoic acid, 4-hydroxy-, carboxymethyl esterHCID 588958052-(2-Hydroxy-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester

Product 1

HCID 671882054-Hydroxy-benzoic acid [2-(4-hydroxy-phenyl)-1-methoxycarbonyl-ethyl carbamoyl]-methoxycarbonylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-hydroxy-benzoic acid carboxymethyl ester 16 (11.8 grams, 60.20 mmol) and 2-(2-hydroxy-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester 3 (15.23 grams, 60.19 mmol) in anhydrous dichloro methane (100 mL) under a nitrogen atmosphere at 0° C. is added to a solution of 1,3-dicyclohexyl carbodiimide (31 grams, 150.24 mmol) in dichloro methane (75 mL) drop wise. 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 17 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 17 which
  6. customcan be purified in an appropriate solvent

Sources & evidence

ORD record
ord-d3933b9c491f4493bcbcc7aa132873a1
Source dataset
uspto-grants-2013_05
Patent number
US08436201B2

Reaction notes

Loading…