Glycine ethyl ester → HCID 605949, compound

HRID 1681339Notes

Reaction equation

HRID 1681339 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@H:7]2[O:9][C@@H:8]2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.[CH2:16]([O:18][C:19](=[O:22])[CH2:20][NH2:21])[CH3:17]>>[CH2:16]([O:18][C:19](=[O:22])[CH2:20][NH:21][CH:7]([C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[CH:8]([OH:9])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:17]

Participants

3

Reactant 2

HCID 12176Glycine ethyl esterHCID 185583(R,R)-Stilbene oxide

Product 1

HCID 605949HCID 605949, compoundYield 69.1%

Procedure

A stirred mixture of trans-stilbene oxide (6.48 g, 0.033 mol), and glycine ethyl ester (6.15 g, 0.0598 mol) was heated at 120° for 22 hours. The mixture was triturated with ether and filtered to remove some insoluble materials. The filtrate was concentrated to yield 6.83 g (69.1%) of oil which solidified into a waxy solid upon cooling. The compound was purified and characterized as the hydrochloride salt, mp 185°-187° C. (absolute ethanolisopropyl ether) [reported mp 167°, Can. J. Chem. 45, 2865 (1967)].

Workup

  1. temperaturewas heated at 120° for 22 hours
  2. customThe mixture was triturated with ether
  3. filtrationfiltered
  4. customto remove some insoluble materials
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9998cd97aed24ed99cab0264eb96c975
Source dataset
uspto-grants-1992_12
Patent number
US05171753

Reaction notes

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