Thiophenol → HCID 21246121, compound

HRID 620425Notes

Reaction equation

HRID 620425 reaction equation
[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7](OS(C1C(C)=CC=CC=1)(=O)=O)=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH3:3].C(N(CC)CC)(C)C.[C:41]1([SH:47])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C=O)C.C(OCC)(=O)C>[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([S:47][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[CH3:3]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 521913N,N-Diethyl-2-propanamineHCID 131712684Benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate

Product 1

HCID 21246121HCID 21246121, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cold, stirring solution of benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (46 mg) in anhydrous DMF (1 ml) is added N-isopropyl-N,N-diethylamine (13 mg) and thiophenol (11 mg). The resulting solution is stirred in the cold for 15 mins. and at room temperature for 45 mins, then diluted with ethyl acetate (10 ml). The mixture is thoroughly washed with water (5×2 ml) and brine, dried with MgSO4, filtered, and evaporated to dryness. The residue is purified on a silica gel GF plate to yield benzyl 6-(1-hydroxyethyl)-3-phenylthio-1-azabicyclo[3.2.0]hept-b 2-en-7-one-2-carboxylate.

Workup

  1. waitand at room temperature for 45 mins
  2. washThe mixture is thoroughly washed with water (5×2 ml) and brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue is purified on a silica gel GF plate
  7. customto yield benzyl 6-(1-hydroxyethyl)-3-phenylthio-1-azabicyclo[3.2.0]hept-b 2-en-7-one-2-carboxylate

Sources & evidence

ORD record
ord-85688b8c1f8642519b59761cb7b863f0
Source dataset
uspto-grants-1989_04
Patent number
US04820817

Reaction notes

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