Methanol → HCID 20550991, compound

HRID 1889054Notes

Reaction equation

HRID 1889054 reaction equation
[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH3:14])=[C:7]2[C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.[CH3:20]O>>[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH3:14])=[C:7]2[C:11]([O:13][CH3:20])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

Product 1

HCID 20550991HCID 20550991, compound

Conditions

Temperature
75 °C

Procedure

7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1 g, 4.67 mmol) was suspended in methanol (20 mL) before treating with conc. sulphuric acid (0.1 ml, 1.876 mmol) and heated at reflux (75° C.) for 16 hours, under argon. After heating for 15 minutes all the remaining solid had dissolved to form a yellow solution. The solution turned from yellow to brown overnight. LCMS run. Desired product seen. Reaction cooled to RT, amount of solvent reduced in vacuo. Residue partitioned between EtOAc (40 ml) and saturated sodium bicarbonate solution (40 ml). Layers separated and aqueous layer was extracted with EtOAc (2×30 ml). Combined extracts were washed with brine (30 ml), dried over Na2SO4, filtered and evaporated to afford a brown gum of the desired product in 801 mg.

Workup

  1. temperatureheated
  2. temperatureAfter heating for 15 minutes all the remaining solid
  3. dissolutionhad dissolved
  4. customto form a yellow solution
  5. customyellow to brown overnight

Sources & evidence

ORD record
ord-600b59e0bef44137a3fe0454068d68f8
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

Loading…