Hydrochloric Acid → HCID 178471404, compound

HRID 1464354Notes

Reaction equation

HRID 1464354 reaction equation
[C:1]([NH:4][C@H:5]([PH:21]([OH:23])=[O:22])[C:6]([CH2:17][CH:18]([CH3:20])[CH3:19])([C:12]([O:14]CC)=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[CH3:2].O.[OH-].[Li+].Cl>O>[C:1]([NH:4][C@H:5]([PH:21]([OH:23])=[O:22])[C:6]([CH2:17][CH:18]([CH3:19])[CH3:20])([C:12]([OH:14])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 178471402HCID 178471402, compound

Product 1

HCID 178471404HCID 178471404, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.02 g of diethyl 2-[(R)-(acetamido)(hydroxyphosphinyl)-methyl]-2-isobutylmalonate were suspended in 20 ml of water and 1.76 g of lithium hydroxide monohydrate were added. The mixture was stirred at room temperature for 3 days and was then acidified by the addition of 6 ml of concentrated hydrochloric acid. The solution was then saturated with sodium chloride and extracted ten times with dichloromethane. The combined extracts were dried over anhydrous magnesium sulfate and evaporated to give 6.0 g of ethyl hydrogen 2-[(R)-(acetamido)(hydroxyphosphinyl)methyl]-2(RS)-isobutylmalonate in the form of a white foam as a 3:1 mixture of diastereoisomers; MS: 324 (M+H)+.

Workup

  1. extractionsaturated with sodium chloride and extracted ten times with dichloromethane
  2. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-73fbfc8f0a12426c958f79202754d855
Source dataset
uspto-grants-1994_04
Patent number
US05304549

Reaction notes

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