Phenylacetyl chloride → HCID 12917426, compound

HRID 1889055Notes

Reaction equation

HRID 1889055 reaction equation
[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH3:15])=[C:7]2[C:11]([O:13][CH3:14])=[O:12].C(N(CC)CC)C.[C:23]1([CH2:29][C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[CH3:15][C:6]1[CH2:5][S:4][CH:3]2[N:8]([C:9](=[O:10])[CH:2]2[NH:1][C:30](=[O:31])[CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:7]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 20550991HCID 20550991, compound

Product 1

HCID 12917426HCID 12917426, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Methyl 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (1126) (801 mg, 3.51 mmol) was dissolved in dry dichloromethane (DCM) (20 mL), cooled to ˜0° C. in an ice bath before adding triethylamine (0.587 mL, 4.21 mmol) followed by phenylacetyl chloride (0.514 mL, 3.86 mmol) in Dichloromethane (DCM) (5 mL) slowly over 5-10 mins. The reaction was then allowed to warm up to RT and stirred for 4 hours then left to stand overnight. LCMS run, desired material seen. Diluted with DCM (40 ml), washed with saturated sodium bicarbonate solution (45 ml). Aqueous layer extracted with DCM (2×30 ml). Combined extracts were washed with brine (45 ml), dried over Na2SO4, filtered and evaporated to afford a red gum of crude material. Purified on a SNAP 100 cartridge, eluting with DCM (3CV) to 100% 10% MeOH in DCM (12CV). Compound identified and solvent removed to afford an orange gum of desired product in 972 mg.

Workup

  1. temperatureto warm up to RT
  2. waitthen left
  3. waitto stand overnight
  4. washwashed with saturated sodium bicarbonate solution (45 ml)
  5. extractionAqueous layer extracted with DCM (2×30 ml)
  6. washCombined extracts were washed with brine (45 ml)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customto afford a red gum of crude material
  11. customPurified on a SNAP 100 cartridge
  12. washeluting with DCM (3CV) to 100% 10% MeOH in DCM (12CV)
  13. customsolvent removed

Sources & evidence

ORD record
ord-eaa9cacf33864c2d859a9abda5c84da7
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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