Triethylamine → HCID 15614706, compound

HRID 620424Notes

Reaction equation

HRID 620424 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].Cl.[CH3:34][N:35]([CH2:37][CH2:38][SH:39])[CH3:36].C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C>[OH:1][CH:2]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([S:39][CH2:38][CH2:37][N:35]([CH3:36])[CH3:34])=[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 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 25798Captamine HydrochlorideHCID 131712684Benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate

Product 1

HCID 15614706HCID 15614706, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (46 mg), 2-(N,N-dimethylamino)ethyl mercaptan hydrochloride (14.2 mg), and triethylamine (14 μl) in anhydrous DMF (2 ml) is stirred at room temperature (25° C.) for 2 hrs. The mixture is added to ethyl acetate (20 ml), washed with 5% sodium bicarbonate (10 ml), water (4×10 ml) and brine, dried over MgSO4, filtered, concentrated in vacuo. Purification of the residue by chromatography on silica gel gives benzyl 6-(1-hydroxyethyl)-3-(2-dimethylaminoethylthio)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

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

Sources & evidence

ORD record
ord-d97ad563f97346ce87eb1375ca20d3bd
Source dataset
uspto-grants-1989_04
Patent number
US04820817

Reaction notes

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