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

HRID 546363Notes

Reaction equation

HRID 546363 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-9c60d4b71d52450095ab5de8f1cc0e42
Source dataset
uspto-grants-2011_05
Patent number
US07935843B2

Reaction notes

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