Dicyclohexylcarbodiimide → N-(1,1dimethylethoxycarbonyl)glycine N-(2-(-(phenylmethoxy)phenyl)ethyl)amide

HRID 53084Notes

Reaction equation

HRID 53084 reaction equation
[CH3:1][C:2]([CH3:12])([O:4][C:5]([NH:7][CH2:8][C:9]([OH:11])=O)=[O:6])[CH3:3].[CH:13]1([N:19]=C=NC2CCCCC2)CCCC[CH2:14]1.[C:28]1([CH2:34][O:35][C:36]2[CH:41]=[CH:40][C:39](CCN)=[CH:38][CH:37]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[C:28]1([CH2:34][O:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:41]=2[CH2:14][CH2:13][NH:19][C:9](=[O:11])[CH2:8][NH:7][C:5]([O:4][C:2]([CH3:1])([CH3:3])[CH3:12])=[O:6])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 2009572-(4-Benzyloxy-phenyl)-ethylamine2×

Product 1

HCID 54004858N-(1,1dimethylethoxycarbonyl)glycine N-(2-(-(phenylmethoxy)phenyl)ethyl)amideYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(1,1-Dimethylethoxycarbonyl)glycine N-(2-(4-phenylmethoxy)phenyl)ethyl)amide. N-(1,1-Dimethylethoxycarbonyl)glycine (850 mg, 4.85 mmol) was stirred with dicyclohexylcarbodiimide (1.00 g, 4.85 mmol) and 2-(4-(phenylmethoxy)phenyl)ethylamine (Intermediate C) (1.00 g, 4.4 mmol) in dry tetrahydrofuran (30 mL) for 16 h. The suspension was filtered and the solvent was evaporated from the filtrate under reduced pressure. The residue was dissolved in ethyl acetate and was washed with aqueous sulphuric acid (10%) and with saturated brine. The solution was dried with anhydrous magnesium sulphate and the solvent was evaporated under reduced pressure to give N-(1,1dimethylethoxycarbonyl)glycine N-(2-(-(phenylmethoxy)phenyl)ethyl)amide (1.65 g, 98%).

Workup

  1. filtrationThe suspension was filtered
  2. customthe solvent was evaporated from the filtrate under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwas washed with aqueous sulphuric acid (10%) and with saturated brine
  5. dry with materialThe solution was dried with anhydrous magnesium sulphate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6078d91084014e80b9e9af5fb94aaee3
Source dataset
uspto-grants-1997_04
Patent number
US05618528

Reaction notes

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