Trifluoroacetic acid water → HCID 131735506, compound

HRID 522174Notes

Reaction equation

HRID 522174 reaction equation
[Si]([O:8][C@@H:9]1[C@H:14]([CH2:15][P:16](=[O:21])([O:19][CH3:20])[O:17][CH3:18])[O:13][C@@H:12]([C:22]([F:25])([F:24])[F:23])[C@H:11]2[O:26]C(C)(C)[O:28][C@@H:10]12)(C(C)(C)C)(C)C.C(O)(C(F)(F)F)=O.O>CCOC(C)=O>[OH:8][C@H:9]1[C@H:10]([OH:28])[C@H:11]([OH:26])[C@H:12]([C:22]([F:24])([F:23])[F:25])[O:13][C@H:14]1[CH2:15][P:16](=[O:21])([O:17][CH3:18])[O:19][CH3:20]

Participants

4

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 131735505HCID 131735505, compound

Product 1

HCID 131735506HCID 131735506, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 25 mL round bottom flask, dimethyl (((3aS,4R,6R,7S,7aR)-7-((tert-butyldimethylsilyl)oxy)-2,2-dimethyl-4-(trifluoromethyl)tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl)methyl)phosphonate (70 mg, 0.14 mmol) was taken up in a TFA-H2O mixture (2 mL, 9:1) at 0° C. The reaction mixture was gradually warmed to rt and stirred at rt for 3 h. Upon completion of the reaction (TLC, 50% EtOAc in hexanes, Rf 0.1), the reaction mixture was concentrated under reduced pressure. The residue obtained was washed with n-pentane (10 mL) to give dimethyl (((2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(trifluoro methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate that was used in next step without purification (40 mg, 88%): 1H NMR (400 MHz, CDCl3) δ 4.54-4.50 (m, 1H), 4.25-4.19 (m, 1H), 4.08-3.97 (m, 2H), 3.77 (d, J=6.0 Hz, 3H), 3.73 (d, J=6.0 Hz, 3H), 3.58-3.54 (m, 1H), 1.58 (s, 3H), 2.44-2.16 (m, 2H); 19F NMR (376.17 MHz, CDCl3) δ −74.36 ppm.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue obtained
  3. washwas washed with n-pentane (10 mL)

Sources & evidence

ORD record
ord-f78a7a33d1064c0d9978e17a04cc6a07
Source dataset
uspto-grants-2016_05
Patent number
US09328134B2

Reaction notes

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