Sodium Bicarbonate → HCID 15117238, compound

HRID 1029629Notes

Reaction equation

HRID 1029629 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH:15]=[C:14]([C:17](=[O:34])[CH2:18][C@H:19]2[NH:22][C:21](=[O:23])[C@@H:20]2[C@H:24]([O:26][Si](C(C)(C)C)(C)C)[CH3:25])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+]>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]=[C:14]([C:17](=[O:34])[CH2:18][C@H:19]2[NH:22][C:21](=[O:23])[C@@H:20]2[C@H:24]([OH:26])[CH3:25])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 15117237HCID 15117237, compound

Product 1

HCID 15117238HCID 15117238, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3S,4R)-4-[2-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-oxoethyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (4.65 g) in acetonitrile (25 ml) was added dropwise boron trifluoride ether complex (2.6 ml) at 0° C., and the mixture was stirred for 1 hour. Sodium hydrogen carbonate (5 g) was added to the reaction mixture, followed by stirring for 30 minutes, and then precipitate was filtered off. Filtrate was dissolved in ethyl acetate (100 ml), washed in turn with water (50 ml) and brine (50 ml), dried over magnesium sulfate. Evaporation of the solvent in vacuo gave (3S,4R)-4-[2-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-oxoethyl]-3-[(1R)-1-hydroxyethyl]-2-oxoazetidine (3.6 g).

Workup

  1. stirringby stirring for 30 minutes
  2. filtrationprecipitate was filtered off
  3. dissolutionFiltrate was dissolved in ethyl acetate (100 ml)
  4. washwashed in turn with water (50 ml) and brine (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-5052d3a78a0b473a910593d1cec8f849
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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