Trifluoroacetic acid → HCID 89614937, compound

HRID 1507752Notes

Reaction equation

HRID 1507752 reaction equation
[CH2:1]([O:8][P:9]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][C:25]([CH3:34])([CH3:33])[C:26]([O:28]C(C)(C)C)=[O:27])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][P:9]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][C:25]([CH3:34])([CH3:33])[C:26]([OH:28])=[O:27])([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117642877HCID 117642877, compound

Product 1

HCID 89614937HCID 89614937, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(3-((bis(benzyloxy)phosphoryl)oxy)propoxy)-2,2-dimethylpropanoate (54) (1.76 g, 3.57 mmol) in DCM (30 mL) was added TFA (1.38 mL, 17.9 mmol), and the reaction was allowed to stir at RT for 4 h. The volatiles were removed in vacuo and the crude product was purified by silica gel chromatography (40 g, 0-30% EtOAc in isohexane (+1% AcOH)) to afford 3-(3-((bis(benzyloxy)phosphoryl)oxy)propoxy)-2,2-dimethylpropanoic acid (55) (1.03 g, 58%) as a colourless oil: m/z 437 (M+H)+ (ES+); 435 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 7.49-7.26 (m, 10H), 5.08-4.95 (m, 4H), 4.03-3.96 (m, 2H), 3.42-3.35 (m, 2H), 3.31 (s, 2H), 1.77 (quin, J=6.2 Hz, 2H), 1.05 (s, 6H).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe crude product was purified by silica gel chromatography (40 g, 0-30% EtOAc in isohexane (+1% AcOH))

Sources & evidence

ORD record
ord-9fb3d2e5b9cb4e4da71d6a70c1d60ad1
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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