Triethylamine → Benzyl 6-azido-3-dipropylamino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1856074Notes

Reaction equation

HRID 1856074 reaction equation
[N:1]([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])=[N+:2]=[N-:3].C(N(CC)CC)C.[CH2:40]([NH:43][CH2:44][CH2:45][CH3:46])[CH2:41][CH3:42]>CN(C)C=O.C(OC(=O)C)C>[N:1]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([N:43]([CH2:44][CH2:45][CH3:46])[CH2:40][CH2:41][CH3:42])=[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])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8902DipropylamineHCID 131711852Benzyl 6-azido-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 23347596Benzyl 6-azido-3-dipropylamino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 6-azido-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (0.1 mmol) in anhydrous dimethylformamide (1 ml) is cooled in an ice-bath and stirred while triethylamine (0.2 mmol) and dipropylamine (0.12 mmol) are added. The resulting solution is allowed to warm to room temperature and kept there overnight. The solution is diluted with ethylacetate, washed with water, pH 3 phosphate buffer, 5% sodium bicarbonate solution, and brine, dried with magnesium sulfate, filtered, and evaporated under vacuum to afford benzyl 6-azido-3-dipropylamino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. additionare added
  2. washwashed with water, pH 3 phosphate buffer, 5% sodium bicarbonate solution, and brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-6e5e3f3198b74de0b0d9fa8a1b8044e1
Source dataset
uspto-grants-1980_08
Patent number
US04217453

Reaction notes

Loading…