Dicyclohexylcarbodiimide → N-(4-(Phenylmethoxy)benzoyl)glycine pentafluorophenyl ester

HRID 53083

Reaction equation

HRID 53083 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]1([CH2:22][O:23][C:24]2[CH:36]=[CH:35][C:27]([C:28]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])=[CH:26][CH:25]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[F:37][C:38]1[C:43](O)=[C:42]([F:45])[C:41]([F:46])=[C:40]([F:47])[C:39]=1[F:48]>O1CCCC1>[F:37][C:38]1[C:43]([O:33][C:32](=[O:34])[CH2:31][NH:30][C:28](=[O:29])[C:27]2[CH:35]=[CH:36][C:24]([O:23][CH2:22][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:25][CH:26]=2)=[C:42]([F:45])[C:41]([F:46])=[C:40]([F:47])[C:39]=1[F:48]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 23931762{[4-(Benzyloxy)phenyl]formamido}acetic acid

Product 1

HCID 53980088N-(4-(Phenylmethoxy)benzoyl)glycine pentafluorophenyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-(4-(Phenylmethoxy)benzoyl)glycine pentafluorophenyl ester. N-(4-(Phenyl-methoxy)benzoyl)glycine methyl ester (14.75 g, 49.2 mmol) was boiled under reflux with methanolic sodium hydroxide (1M) (80 mL) for 2 h. The solvent was evaporated under reduced pressure. The residue was dissolved in water and was acidified by addition of aqueous hydrochloric acid. The suspension was extracted with ethyl acetate. The extract was washed with saturated brine and was dried with anhydrous magnesium sulphate. The solvent was evaporated under reduced pressure to give N-(4-(phenylmethoxy)benzoyl)glycine (6.59 g, 47%). Dicyclohexylcarbodiimide (720 mg, 3.5 mmol) was added to N-(4-(phenylmethoxy)benzoyl)glycine (100 g, 3.5 mmol) in dry tetrahydrofuran (100 mL) and the mixture was taken to 0° C. Pentafluorophenol (640 g, 3.5 mmol) was added dropwise and the mixture was stirred for 17 h at 0° C. The suspension was filtered and the solvent was evaporated from the filtrate under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and was washed with saturated aqueous sodium hydrogen carbonate (2×75 mL), with aqueous sulphuric acid (10%) and with water. The solution was dried with anhydrous magnesium sulphate and the solvent was evaporated under reduced pressure to give N-(4-(phenylmethoxy)benzoyl)glycine pentafluorophenyl ester (Intermediate B) (1.5 g, 95%).

Workup

  1. customwas taken to 0° C
  2. filtrationThe suspension was filtered
  3. customthe solvent was evaporated from the filtrate under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  5. washwas washed with saturated aqueous sodium hydrogen carbonate (2×75 mL), with aqueous sulphuric acid (10%) and with water
  6. dry with materialThe solution was dried with anhydrous magnesium sulphate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-784808cf7bea43ebb9b6631dba0951b5
Source dataset
uspto-grants-1997_04
Patent number
US05618528

Linked notes

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