Trifluoroacetic acid → azetidin-3-ylmethyl dimethylphosphinate TFA salt

HRID 1039981Notes

Reaction equation

HRID 1039981 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][P:9]([O:12][CH2:13][CH:14]1[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]1)([CH3:11])=[O:10]>ClCCl>[OH:5][C:3]([C:2]([F:7])([F:6])[F:1])=[O:4].[CH3:8][P:9]([CH3:11])(=[O:10])[O:12][CH2:13][CH:14]1[CH2:17][NH:16][CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67431958Tert-butyl 3-{[(dimethylphosphoryl)oxy]methyl}azetidine-1-carboxylate

Product 1

HCID 131730894azetidin-3-ylmethyl dimethylphosphinate TFA salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (120 mL) was added dropwise to the product of Step 1 (80 g) in dichloromethane (120 mL) at 0° C. over a period of 30 min. The reaction mixture was stirred at room temperature for 2 h. After completion of reaction, reaction mixture was concentrated to remove excess trifluoroacetic acid under vacuum to afford azetidin-3-ylmethyl dimethylphosphinate TFA salt (90 g) as brown liquid. LC ESI: [M+H]+ m/z 164.2; HPLC purity; >97%. 1H NMR (400 MHz, CD3OD) S: 1.62 (s, 3H), 1.65 (s, 3H), 3.23-3.27 (m, 1H), 4.02 (dd, J=7.7, 11.1 Hz, 2H), 4.11-4.19 (m, 4H).

Workup

  1. customAfter completion of reaction, reaction mixture
  2. concentrationwas concentrated
  3. customto remove excess trifluoroacetic acid under vacuum

Sources & evidence

ORD record
ord-04f4fad0ae894056a419e6e77e67a4ab
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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