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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 29744Generated: October 25, 2026

Lithium Hydroxide → 2-[(1-Benzyloxycarbonylamino-2-methyl-propyl)-hydroxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acid

https://huagongshe.com/reaction/29744

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium HydroxideHCID 3939—
Reactant2-[(1-Benzyloxycarbonylamino-2-methylpropyl)-methoxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acid methyl esterHCID 54392018—
SolventAcetonitrileHCID 6342—
Product2-[(1-Benzyloxycarbonylamino-2-methyl-propyl)-hydroxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acidHCID 17904703102.3%

Reaction Conditions

Temperature50 °C

Reaction Steps

1 M LiOH (5 mL) was added to a solution of 2-[(1-benzyloxycarbonylamino-2-methylpropyl)-methoxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acid methyl ester (187 mg, 0.35 mmol) in acetonitrile (5 mL). The mixture was stirred at 50° C. over night and concentrated under reduced pressure. The crude product was purified using chromathography (iPrOH/conc. aq. NH3/H2O, 4:2:1) to yield 2-[(1-benzyloxycarbonylamino-2-methyl-propyl)-hydroxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acid (180 mg, 100%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07423012B2
Source datasetuspto-grants-2008_09
ORD IDord-b1dee656e0d746948a97118af01a44d1
Source noteuspto-grants-2008_09