Formic Acid → HCID 19815407, compound

HRID 466440Notes

Reaction equation

HRID 466440 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[CH3:2].[CH:23](O)=[O:24]>C1(C)C(C)=CC=CC=1>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[CH:23]=[O:24])[CH3:2]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 19815326HCID 19815326, compound

Product 1

HCID 19815407HCID 19815407, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 5.83 g of N-(4-benzyloxybenzyl)glycine ethyl ester, 0.86 mL of formic acid, and 20 mL of xylene was refluxed for 2 hours using a Dean-Stark trap to remove the water produced in the reaction. After cooling, the reaction mixture was washed with 20% aqueous formic acid, water, saturated sodium bicarbonate solution, water, and brine. Finally the mixture was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to furnish 6.23 g of crude N-(4-benzyloxybenzyl)-N-formyl glycine ethyl ester, used in the following reaction without further purification.

Workup

  1. customto remove the water
  2. customproduced in the reaction
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with 20% aqueous formic acid, water, saturated sodium bicarbonate solution, water, and brine
  5. dry with materialFinally the mixture was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dfcdd1c861904528968911c682ac1887
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

Loading…