Ammonium Chloride → HCID 86672800, compound

HRID 1755125Notes

Reaction equation

HRID 1755125 reaction equation
[C:1]([Si:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:6][CH2:7][CH2:8][C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[O:11][C@@H:10]1[CH2:16][OH:17])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[O:39](S(C(F)(F)F)(=O)=O)[S:40]([C:43]([F:46])([F:45])[F:44])(=O)=[O:41].[Cl-].[NH4+]>ClCCl>[C:1]([Si:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:6][CH2:7][CH2:8][C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[O:11][C@@H:10]1[CH2:16][O:17][S:40]([C:43]([F:46])([F:45])[F:44])(=[O:41])=[O:39])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 59467105HCID 59467105, compound

Product 1

HCID 86672800HCID 86672800, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{(4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol (159 mg, 0.38 mmol) was dissolved in dichloromethane (1.15 mL). Diisopropylethylamine (200 μL, 1.15 mmol) and Tf2O (77.4 μL, 0.46 mmol) were added at 0° C., and the mixture was stirred at room temperature for one hour in a nitrogen atmosphere. Saturated aqueous ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give trifluoro-methanesulfonic acid (4R,5S)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester as a crude product.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3c165d6924304c6ab9ee43308d926932
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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