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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1480933Generated: October 30, 2026

Methanol → 2-(S)-Hydroxy-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acid

https://huagongshe.com/reaction/1480933

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantL-IsoserineHCID 6999797—
ReactantMethyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylateHCID 86709142—
SolventSodium MethoxideHCID 10942334—
Product2-(S)-Hydroxy-3-[(4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]propionic acidHCID 7173514093.5%

Reaction Steps

A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (90 mg, 0.31 mmol) and 2-(S)-hydroxy-3-amino-propionic acid (Sigma-Aldrich) (96 mg, 0.92 mmol) in 0.5 N NaOMe in MeOH solution (1.22 mL, 0.61 mmol) was microwaved at 120° C. for 1 h and concentrated. Residue was dissolved in water (70 mL) and acidified by 1 N HCl solution to pH=3-4. It was extracted with EtOAc, Organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give the title compound (105 mg, 0.29 mmol) in 92% yield. LC-MS ESI−: 366.99 (M−1)−.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09409892B2
Source datasetuspto-grants-2016_08
ORD IDord-316329ae4d7643ca975d302c89961bdf
Source noteuspto-grants-2016_08