isobutyl P-(3-t-butoxycarbonylamino-2-oxo-propyl)-P-(methyl)-phosphinate → Phosphinic acid, (3-amino-2-oxopropyl)methyl-

HRID 1198816Notes

Reaction equation

HRID 1198816 reaction equation
C(OC([NH:8][CH2:9][C:10](=[O:20])[CH2:11][P:12]([CH3:19])(=[O:18])[O:13]CC(C)C)=O)(C)(C)C>Cl>[NH2:8][CH2:9][C:10](=[O:20])[CH2:11][P:12]([CH3:19])(=[O:13])[OH:18]

Participants

3

Reactant 1

HCID 23374770isobutyl P-(3-t-butoxycarbonylamino-2-oxo-propyl)-P-(methyl)-phosphinate

Product 1

HCID 10261259Phosphinic acid, (3-amino-2-oxopropyl)methyl-

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 0.5 g of isobutyl P-(3-tert.-butoxycarbonylamino-2-oxo-propyl)-P-methyl-phosphinate in 10 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 4 hours. The mixture is then allowed to cool to room temperature, concentrated under reduced pressure, and co-evaporated twice with 20 ml of water. The crude product is dissolved in 20 ml of ethanol, 1 ml of propylene oxide is added, and the mixture is stirred until the precipitated solid is free of halogen. The solid is filtered and dried to give P-(3-amino-2-oxo-propyl)-P-methyl-phosphinic acid, m.p. 148°-149°, 31P-NMR spectrum: δ=32.8 ppm (D2O).

Workup

  1. temperatureto reflux for a period of 4 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude product is dissolved in 20 ml of ethanol
  4. addition1 ml of propylene oxide is added
  5. filtrationThe solid is filtered
  6. customdried

Sources & evidence

ORD record
ord-5382fad75de54680ae85eae74412745e
Source dataset
uspto-grants-1994_01
Patent number
US05281747

Reaction notes

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