Diethyl vinylphosphonate → HCID 10903865, compound

HRID 849278Notes

Reaction equation

HRID 849278 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:13]([P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])=[CH2:14]>CO>[CH2:17]([O:16][P:15]([CH2:13][CH2:14][NH:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:22])[O:19][CH2:20][CH3:21])[CH3:18]

Participants

4

Reactant 2

HCID 69629Diethyl vinylphosphonateHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 10903865HCID 10903865, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(t-butyloxycarbonylamino) propanamine (77 g, 0.44 mole) in methanol (500 mL) was added diethyl vinylphosphonate 97% (75 g, 0.44 mole; Aldrich 11, 613-0) under nitrogen and kept in a water bath at ~20° C. for 48 hr. The reaction mixture was concentrated in vacua and the residue (~160 g) was put on a pad of "Florisil" (3"×6") and eluted with methylene chloride/hexane 1:1, methylene chloride and finally 10% methanol/methylene chloride to give the title compound as a colorless oil (121 g, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacua
  2. washeluted with methylene chloride/hexane 1:1, methylene chloride and finally 10% methanol/methylene chloride

Sources & evidence

ORD record
ord-636a50876eba4c63b43dc697d15d5c6d
Source dataset
uspto-grants-2000_01
Patent number
US06011168

Reaction notes

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