Greatly simplified procedures for the synthesis of α-amino acids by the direct alkylation of pseudoephedrine glycinamide hydrate

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 3322-3327

  Myers, Andrew G ^a,b   Schnider, Patrick ^a   Kwon, Soojin ^a   Kung, Daniel W ^a  

^a California Institute of Technology   (United States)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; GLYCINAMIDE; PSEUDOEPHEDRINE;

ALKYLATION; AMINO ACID SYNTHESIS; ARTICLE; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033617465     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990341z     Document Type: Article

References (9)

1. (a) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488.
2. (b) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656.
3. Myers, A. G.; Yoon, T.; Gleason, J. L. Tetrahedron Lett. 1995, 36, 4555.
4. This procedure is also effective for the preparation of pseudoephedrine sarcosinamide (nonhydrated), in 71% yield (from sarcosine hydrochloride) after recrystallization from toluene.
5. Seebach and co-workers have previously shown that lithium halides can increase the solubility of peptides in ethereal solvents by as much as 100-fold; see: Seebach, D.; Thaler, A.; Beck, A. K. Helv. Chim. Acta 1989, 72, 857.
6. Einhorn, J.; Luche, J. L. J. Org. Chem. 1987, 52, 4124.
7. 5
8. Prolonged (> 1 d) drying in vacuo (0.5 mmHg) may cause partial dehydration of the product. Rehydration occurs upon exposure to the atmosphere.
9. 5