Triethylamine → HCID 19815326, compound

HRID 466439Notes

Reaction equation

HRID 466439 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(N(CC)CC)C.[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O.C(OCC)C>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:25][CH:26]=1)[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 700424-Benzyloxybenzyl chlorideHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 19815326HCID 19815326, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 11.0 g of glycine ethyl ester hydrochloride in 100 mL of dimethylformamide at 25° was added 22.0 mL of triethylamine. To the resulting milky suspension was added 9.08 g of 4-benzyloxybenzyl chloride in 50 mL of DMF dropwise over 0.5 hour. The mixture was stirred for 16 hours at 25°. The reaction mixture was diluted with diethyl ether and then filtered to remove the precipitated triethylamine hydrochloride. The resulting solution was concentrated in vacuo, and the residue was dissolved in ethyl acetate. The solution was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Kugelrohr distillation provided 5.90 g of N-(4-benzyloxybenzyl)glycine ethyl ester [bp 160°-180° (0.015 torr.)]; NMR (200 MHz, CDCl3): δ 7.43-7.27 (m, 5H); 7.06 (A2B2, 4H); 5.01 (s, 2H); 4.14 (quart., 2H); 3.71 (s, 2H); 3.36 (s, 3H); 2.01 (bs, 1h); 1.24 (t, 3H).

Workup

  1. filtrationfiltered
  2. customto remove the precipitated triethylamine hydrochloride
  3. concentrationThe resulting solution was concentrated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-1a05d53587b543ea9d3fecc056ab7b2d
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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