Triethylamine → Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-(2-dimethylaminoethylthio)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1252764Notes

Reaction equation

HRID 1252764 reaction equation
[F:1][C:2]([F:35])([F:34])[CH:3]([CH:5]1[C:11](=[O:12])[N:10]2[CH:6]1[CH2:7][C:8](OS(C1C(C)=CC=CC=1)(=O)=O)=[C:9]2[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[OH:4].Cl.[CH3:37][N:38]([CH2:40][CH2:41][SH:42])[CH3:39].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]([F:35])([F:34])[CH:3]([CH:5]1[C:11](=[O:12])[N:10]2[CH:6]1[CH2:7][C:8]([S:42][CH2:41][CH2:40][N:38]([CH3:39])[CH3:37])=[C:9]2[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[OH:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 25798Captamine HydrochlorideHCID 131714283Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 14156081Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-(2-dimethylaminoethylthio)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (51 mg), 2-(N,N-dimethylamino)ethylmercaptan hydrochloride (14.2 mg), and triethylamine (14 ml) in anhydrous DMF (2 ml) is stirred at room temperature for 2 hours. The mixture is diluted with ethyl acetate (20 ml), washed with 5% sodium bicarbonate (2×5 ml), water (4×10 ml), and brine, dried with MgSO4, filtered, and concentrated in vacuo. The residue is purified by chromatography on silica gel to yield benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-(2-dimethylaminoethylthio)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. washwashed with 5% sodium bicarbonate (2×5 ml), water (4×10 ml), and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d3ce5213af3e473da382bc1d2fd46900
Source dataset
uspto-grants-1988_05
Patent number
US04745188

Reaction notes

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