3,4,5-Trimethoxybenzaldehyde → (2S)-2-Amino-3-(3,4,5-trimethoxyphenyl)propanoic acid

HRID 1920623Notes

Reaction equation

HRID 1920623 reaction equation
COC1C=C(C=C(OC)C=1OC)C=O.C(NCC(O)=O)(=O)C.C[O:24][C:25](=[O:44])[C@H:26]([CH2:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[C:34]([O:42][CH3:43])[CH:33]=1)[NH:27]C(=O)C>>[NH2:27][C@@H:26]([CH2:31][C:32]1[CH:33]=[C:34]([O:42][CH3:43])[C:35]([O:40][CH3:41])=[C:36]([O:38][CH3:39])[CH:37]=1)[C:25]([OH:44])=[O:24]

Participants

4

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 10972AcetylglycineHCID 67492543racemic N-acetyl-3,4,5-trimethoxy-phenylalanine methyl ester

Product 1

HCID 21107851(2S)-2-Amino-3-(3,4,5-trimethoxyphenyl)propanoic acid

Procedure

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).

Sources & evidence

ORD record
ord-5548d2310a84495aafc9dd3e43774de9
Source dataset
uspto-grants-2012_05
Patent number
US08173128B2

Reaction notes

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