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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 455310Generated: October 30, 2026

Hydrochloric Acid → 8-(benzyloxy)-5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-1,6-naphthyridine-7-carboxylic acid

https://huagongshe.com/reaction/455310

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantEthyl AcetateHCID 8857—
ReactantSodium HydroxideHCID 14798—
ReactantMethyl 8-(benzyloxy)-5-(5-(tert-butoxycarbonylamino)-N-methylpentyl-sulfonamido)-1,6-naphthyridine-7-carboxylateHCID 67109489—
SolventMethanolHCID 887—
SolventWaterHCID 962—
Product8-(benzyloxy)-5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-1,6-naphthyridine-7-carboxylic acidHCID 6710992994%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a solution of methyl 8-(benzyloxy)-5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-1,6-naphthyridine-7-carboxylate (Example 2.3; 4.05 mmol) in methanol (8 ml) and water (8 ml) at rt was added sodium hydroxide (16.2 mmol). The reaction was heated at 50° C. Ethyl acetate was added and the aquous phase was treated with HCl 1N until pH=6-7. Ethyl acetate was added again, the layers were separated and the organic phase was dried with MgSO4 and concentrated. The crude product was obtained in 94% yield, and used in the next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08497270B2
Source datasetuspto-grants-2013_07
ORD IDord-9ffde3371a5d4f449f64c84dd4a7065e
Source noteuspto-grants-2013_07