Sodium Carbonate → HCID 70488443, compound

HRID 1719706Notes

Reaction equation

HRID 1719706 reaction equation
F.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][N:8]=[C:7]2[N:16]1[CH2:21][CH2:20][C@@H:19]([CH:22]([CH3:31])[CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][S:25]2(=[O:30])=[O:29])[C@H:18]([O:32][Si](C(C)(C)C)(C)C)[CH2:17]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][N:8]=[C:7]2[N:16]1[CH2:21][CH2:20][C@@H:19]([CH:22]([CH3:31])[CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][S:25]2(=[O:29])=[O:30])[C@H:18]([OH:32])[CH2:17]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 14917Hydrofluoric AcidHCID 131714326HCID 131714326, compound

Product 1

HCID 70488443HCID 70488443, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

40% Aqueous hydrofluoric acid (0.5 cm3) was added at room temperature to a stirred solution of trans-2-{2-[1-(6,7-dimethoxyquinazolin-4-yl)-3-t-butyldimethylsilyloxypiperid-4-yl]prop-1-yl}isothiazolidine-1,1-dioxide (diastereomer A; 0.64 g) in acetonitrile (7.0 cm3). After stirring for 16 hours aqueous saturated sodium carbonate solution (5 cm3) was added and the residue was partitioned between water (10 cm3) and chloroform (60 cm3). The dried (MgSO4) organic layer was evaporated and the residue was chromatographed on silica ("Merck" 60.9385) eluting with chloroform to afford a foam which crystallised from ethyl acetate to give trans-2-{2-(1-[6,7-dimethoxy quinazolin-4-yl]-3-hydroxypiperid-4-yl)prop-1-yl}isothiazolidine-1,1-dioxide as microcrystals (diastereomer A) m.p. 173°-174° (0.394 g).

Workup

  1. additionwas added
  2. customthe residue was partitioned between water (10 cm3) and chloroform (60 cm3)
  3. dry with materialThe dried (MgSO4) organic layer
  4. customwas evaporated
  5. customthe residue was chromatographed on silica ("Merck" 60.9385)
  6. washeluting with chloroform
  7. customto afford a foam which
  8. customcrystallised from ethyl acetate

Sources & evidence

ORD record
ord-b82658248618475f84fcd9846b0acde0
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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