Sodium benzenethiolate → HCID 85749743, compound

HRID 838889Notes

Reaction equation

HRID 838889 reaction equation
Br[CH2:2][CH:3]1[O:9][CH:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[CH2:4]1.[C:11]1([S-:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:11]1([S:17][CH2:2][CH:3]2[O:9][CH:8]3[N:5]([C:6](=[O:10])[CH2:7]3)[CH2:4]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 4110039Sodium benzenethiolateHCID 19602500HCID 19602500, compound

Product 1

HCID 85749743HCID 85749743, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

(3RS, 5SR)-3-Bromomethyl-4-oxa-1-azabicyclo[3.2.0]heptan-7-one (210 mg, 1.0 mmole) in dry dimethylformamide (2 ml) was added dropwise to a stirred solution of sodium thiophenolate (1.2 mmole) in dry DMF (5 ml). The solution was stirred at room temperature with exclusion of moisture for 16 hours and was then diluted with ethyl acetate (30 ml). The solution was washed three times with water, dried, and the solvent removed to give a colourless oil. The oil was chromatographed on silica gel (15 g) using ethyl acetate/petroleum ether to give the title compound as a colourless gum (205 mg, 87%). (Found : M+, 235.06551. C12H13NO2S requires 235.06669. νmax (CHCl3) 1785 (β-lactam C=O)cm-1 δ p.p.m. (CDCl3) 2.6 - 3.5 [complex, 5H, C(6)H2, C(2)H, CH2SPh[; 4.10 [dd, J 11.5Hz, J' 6Hz, 1H, C(2)H]; 4.52 [quin., J 6Hz, 1H, C(3)H]; 5.43 [d, J 2.5Hz, 1H, C(5)H]; 7.48 (5H, aromatic H). m/e : 235 (M+, 100%), 192 (30), 123 (71).

Workup

  1. washThe solution was washed three times with water
  2. customdried
  3. customthe solvent removed
  4. customto give a colourless oil
  5. customThe oil was chromatographed on silica gel (15 g)

Sources & evidence

ORD record
ord-5b288db36161400a9f11a5bb5bd31ee2
Source dataset
uspto-grants-1978_06
Patent number
US04093626

Reaction notes

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