Sodium Bicarbonate → HCID 70236275, compound

HRID 727110Notes

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

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/Na2 SO4 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/Na2 SO4
customthen evaporated
extractionthen extracted with chloroform
dry with materialThe organic phase was dried over NaCl/Na2SO4
customthen evaporated

Sources & evidence

ORD record: ord-c91235d1a6ef4bf7ac5ee3ec819e6ef3
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712287

Reaction notes

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