Sodium Bicarbonate → HCID 70236275, compound
Reaction equation
[C:1]([CH:4]([CH:6]([C:8]([OH:10])=[O:9])[OH:7])O)(O)=O.C(S[C:16]1[C:20]([C@@H:21]2[CH2:27][N:26]3[CH2:28][C@H:22]2[CH2:23][CH2:24][CH2:25]3)=[N:19][S:18][N:17]=1)CCC.C([O-])(O)=[O:30].[Na+].O[O:35][S:36]([O-:38])=O.[K+]>O>[C:8]([OH:10])(=[O:9])[C:6]([OH:30])=[O:7].[CH2:1]([S:36]([C:16]1[C:20]([C@@H:21]2[CH2:27][N:26]3[CH2:28][C@H:22]2[CH2:23][CH2:24][CH2:25]3)=[N:19][S:18][N:17]=1)(=[O:38])=[O:35])[CH2:4][CH2:6][CH3:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of (5S,6S)-6-(3-butylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane tartrate (Compound 111) (4.4 g, 10.1 mmol) in water was treated with saturated aqueous NaHCO3 until basic then extracted with ethyl acetate (3×100 ml). The organic phase was dried over NaCl/Na2SO4 then evaporated. The residue was taken up in 1N HCl(aq) and water (23 ml) and cooled to 0° C. A solution of oxone (9.2 g, 15.0 mmol) in water (45 ml) was added dropwise to the reaction then stirred overnight at room temperature. The pH of the reaction was adjusted to 9 then extracted with chloroform. The organic phase was dried over NaCl/Na2SO4 then evaporated to yield 3.9 g of free base. Crystallization with oxalic acid gave the title compound. (Compound 129). M.p. 147-151° C.
Workup
- extractionthen extracted with ethyl acetate (3×100 ml)
- dry with materialThe organic phase was dried over NaCl/Na2SO4
- customthen evaporated
- extractionthen extracted with chloroform
- dry with materialThe organic phase was dried over NaCl/Na2SO4
- customthen evaporated
Sources & evidence
- ORD record
- ord-795f95a01d7241c09c478712d0d424b2
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06271229B1
Reaction notes
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