Trifluoroacetic acid → 3-(2-(2-((Bis(benzyloxy)phosphoryl)oxy)ethoxy)ethoxy)-2,2-dimethylpropanoic acid

HRID 1507750Notes

Reaction equation

HRID 1507750 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([O:15][P:16]([O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][C:34]([CH3:43])([CH3:42])[C:35]([O:37]C(C)(C)C)=[O:36])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([O:15][P:16]([O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][C:34]([CH3:43])([CH3:42])[C:35]([OH:37])=[O:36])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117642919tert-Butyl 3-(2-(2-((bis(benzyloxy)phosphoryl)oxy)ethoxy)ethoxy)-2,2-dimethylpropanoate

Product 1

HCID 896148853-(2-(2-((Bis(benzyloxy)phosphoryl)oxy)ethoxy)ethoxy)-2,2-dimethylpropanoic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (6.63 mL, 86 mmol) was added dropwise to a stirred solution of tert-butyl 3-(2-(2-((bis(benzyloxy)phosphoryl)oxy)ethoxy)ethoxy)-2,2-dimethylpropanoate (50) (4.5 g, 8.61 mmol) in DCM (43 mL) and the reaction mixture was allowed to stir at RT for 16 h then concentrated in vacuo. The crude product was dissolved in EtOAc (150 mL) and washed with 1M HCl (aq.) (50 mL), water (2×50 mL), and brine (50 mL) the organic layer was dried (MgSO4), filtered and concentrated in vacuo to afford 3-(2-(2-((bis(benzyloxy)phosphoryl)oxy)ethoxy)ethoxy)-2,2-dimethylpropanoic acid (51) (3.98 g, 99%) as a colourless oil: m/z 467 (M+H)+ (ES+); 465 (M−H)− (ES−). 1H NMR (400 MHz, CDCl3) δ: 7.36-7.31 (m, 10H), 5.12-5.03 (m, 4H), 4.14-4.09 (m, 2H), 3.69-3.64 (m, 2H), 3.60 (s, 4H), 3.47 (s, 2H), 1.20 (s, 6H).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe crude product was dissolved in EtOAc (150 mL)
  3. washwashed with 1M HCl (aq.) (50 mL), water (2×50 mL), and brine (50 mL) the organic layer
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34c32737a8b844b595b5bf8dc8a54eac
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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