Bromotrimethylsilane → HCID 86746588, compound

HRID 1612763Notes

Reaction equation

HRID 1612763 reaction equation
C(OC([NH:8][CH2:9][C:10](=[O:21])[CH2:11][P:12]([CH2:17][CH2:18][CH2:19][CH3:20])(=[O:16])[O:13]CC)=O)(C)(C)C.C[Si](C)(C)[Br:24]>ClCCl.CO.O>[BrH:24].[NH2:8][CH2:9][C:10](=[O:21])[CH2:11][P:12]([CH2:17][CH2:18][CH2:19][CH3:20])(=[O:13])[OH:16]

Participants

6

Reactant 2

HCID 76113BromotrimethylsilaneHCID 9996173HCID 9996173, compound

Product 1

HCID 86746588HCID 86746588, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.642 g of ethyl 3-(N-tert.-butoxycarbonylamino)-2-oxo-propyl(n-butyl)phosphinate in 10 ml of anhydrous dichloromethane under an inert atmosphere is treated with 1.53 g of trimethylbromosilane. After stirring for 7 hours at room temperature the volatile material is removed in vacuo to afford a pale yellow oil. This oil is dissolved in methanol containing 1% of water, and the clear pale yellow solution is stirred overnight at room temperature. The solvent is removed in vacuo to afford 3-amino-2-oxo-propyl(n-butyl)phosphinic acid hydrobromide, m.p. 135°-138°. Suspension in ethanol and treatment with propylene oxide affords 3-amino-2-oxo-propyl(n-butyl)phosphinic acid of m.p. 128°-130°.

Workup

  1. customis removed in vacuo
  2. customto afford a pale yellow oil
  3. stirringthe clear pale yellow solution is stirred overnight at room temperature
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-aa19d5335dce454db710535d908f70ba
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

Loading…