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D,L-threo-Droxidopa Hydrochloride

D,L-threo-Droxidopa Hydrochloride is a stereoisomeric impurity arising from the racemic synthesis of Droxidopa, featuring a threo configuration with (2R,3R)/(2S,3S) diastereomerism. Its structure incorporates a 3,4-dihydroxyphenylproline scaffold, protonated at the amino group via hydrochloride salt formation. The compound exhibits enantiomeric purity challenges due to its chiral centers, necessitating chromatographic resolution. This impurity is critical as an HPLC reference standard for quantifying enantiomeric deviations in Droxidopa active pharmaceutical ingredient batches.

On Request
Molecular Formula C23H24ClNO5
Molecular Weight 429.9000
CAS Number 73594-43-1 ✓ Verified
PubChem CID 13279814 ↗
Purity N/A
Product Type API Impurity
Parent Drug Droxidopa
Lead Time On Request
IUPAC Name (2S,3R)-2-amino-3-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxypropanoic acid;hydrochloride

📝 Synonyms

73594-43-1 3,4-Di-O-benzyl DL-threo-Droxidopa Hydrochloride (2S,3R)-2-amino-3-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxypropanoic acid;hydrochloride DL-threo-3-[3,4-Bis(benzyloxy)phenyl)serine Hydrochloride; beta-Hydroxy-3-(phenylmethoxy)-O-(phenylmethyl)-threo-DL-tyrosine Hydrochloride; DTXSID90534304 (betaR)-O-Benzyl-3-(benzyloxy)-beta-hydroxy-L-tyrosine--hydrogen chloride (1/1)

🔬 Chemical Identifiers

C1=CC=C(C=C1)COC2=C(C=C(C=C2)[C@H]([C@@H](C(=O)O)N)O)OCC3=CC=CC=C3.Cl
InChI=1S/C23H23NO5.ClH/c24-21(23(26)27)22(25)18-11-12-19(28-14-16-7-3-1-4-8-16)20(13-18)29-15-17-9-5-2-6-10-17;/h1-13,21-22,25H,14-15,24H2,(H,26,27);1H/t21-,22+;/m0./s1
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