Sodium Bicarbonate → 2-(1-Fluoro 2-propynyl)-4-thiazolemethanol
Reaction equation
[F-:1].[F-].[F-].C(N(SN(CC)CC)CC)C.[C:15]([CH:17]([C:19]1[S:20][CH:21]=[C:22]([CH2:24][O:25]C2CCCCO2)[N:23]=1)O)#[CH:16].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][CH:17]([C:19]1[S:20][CH:21]=[C:22]([CH2:24][OH:25])[N:23]=1)[C:15]#[CH:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -55 °C
Procedure
0.53 ml of diethylaminosulfide trifluoride (DAST) were added at about -60° C. to a solution of 1 g of the product of Stage C and 5 ml of methylene chloride and the reaction mixture was stirred for 2 hours at -55° C. and poured into a solution of sodium bicarbonate. Extraction was carried out with methylene chloride and the extracts were dried over magnesium sulfate, filtered and evaporated to dryness. The residue was taken up in 5 ml of methanol and 20 mg of toluene-sulfonic acid were added. The reaction mixture was stirred for one hour at 20° C., followed by evaporation to dryness. The residue was chromatographed on silica eluting with a hexane-ethyl acetate mixture (7-3) to obtain 0.16 g of the desired product with a Rf=0.10.
Workup
- extractionExtraction
- dry with materialthe extracts were dried over magnesium sulfate
- filtrationfiltered
- customevaporated to dryness
- addition20 mg of toluene-sulfonic acid were added
- stirringThe reaction mixture was stirred for one hour at 20° C.
- customfollowed by evaporation to dryness
- customThe residue was chromatographed on silica eluting with a hexane-ethyl acetate mixture (7-3)
Sources & evidence
- ORD record
- ord-28169f9ea77941eea284bc7229c3d666
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05395845
Reaction notes
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