Hydrofluoric Acid → HCID 86747488, compound

HRID 1197928Notes

Reaction equation

HRID 1197928 reaction equation
[O:1]([C@@H:9]([CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32])[C@@H:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[Si](C(C)(C)C)(C)C.F.C(=O)(O)[O-].[Na+]>C(#N)C>[CH:12]1([CH2:11][C@H:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[C@@H:9]([OH:1])[CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][C:28]2=[O:32])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 57180353HCID 57180353, compound

Product 1

HCID 86747488HCID 86747488, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 178435178HCID 178435178, compoundSolvent

Procedure

0.62 g (1.28 mmol) of t-butyl [(1S,2S)-2-(t-butyldimethylsiloxy)-1-(cyclohexylmethyl)-3-(2-oxo-1-pyrrolidinyl)propyl]carbamate was dissolved in 9 ml of acetonitrile in a polypropylene reaction vessel and treated at room temperature with 1.2 ml of 40% aqueous hydrofluoric acid. The reaction mixture was subsequently stirred at room temperature for 3 hours, thereafter poured into 2N sodium bicarbonate solution and extracted with methylene chloride. The methylene chloride extracts were dried over magnesium sulfate and evaporated under reduced pressure, whereby there were obtained 434 mg of t-butyl [(1S,2S)-1-(cyclohexylmethyl)-2-hydroxy-3-(2-oxo-1-pyrrolidinyl)propyl]carbamate as an oil which was used directly in the next step.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe methylene chloride extracts were dried over magnesium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-589e8dbc24544d2e864d7e65a7cdec62
Source dataset
uspto-grants-1994_01
Patent number
US05278148

Reaction notes

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