HuagongsheHuagongshe Chemistry Print Report · For research reference only
3,4,5-Trimethoxybenzaldehyde → (2S)-2-Amino-3-(3,4,5-trimethoxyphenyl)propanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3,4,5-Trimethoxybenzaldehyde | HCID 6858 | — |
| Reactant | Acetylglycine | HCID 10972 | — |
| Reactant | racemic N-acetyl-3,4,5-trimethoxy-phenylalanine methyl ester | HCID 67492543 | — |
| Product | (2S)-2-Amino-3-(3,4,5-trimethoxyphenyl)propanoic acid | HCID 21107851 | — |
Reaction Steps
The title compound is prepared from commercially available 3,4,5-trimethoxybenzaldehyde and N-acetylglycine according to a literature procedure (E.M. Oltz, R. C. Bruening, M. J. Smith, K. Kustin and K. Nakanishi in J. Am. Chem. 1998, 110 (18), 6162-6172). The resolution of the racemic N-acetyl-3,4,5-trimethoxy-phenylalanine methyl ester is performed by enzyme-catalyzed hydrolysis of the L-ester using Alcalase® (Novo Nordisk) as described in the literature (J. J. Nestor, Jr., T. L. Ho, R. A. Simpson, B. L. Horner, G. H. Jones, G. I. McRae and B. H. Vickery in J. Med. Chem. 1982, 25 (7), 795-801; or O. D. Tyagi & P. M. Boll in Indian J. Chem. 1992, pp. 851-854).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173128B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-5548d2310a84495aafc9dd3e43774de9 |
| Source note | uspto-grants-2012_05 |