Dimethylformamide → HCID 13389336, compound

HRID 2295319Notes

Reaction equation

HRID 2295319 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].[CH2:33]([N:35]([CH2:38]C)[CH2:36]C)[CH3:34].[CH3:40][N:41](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]([N:41]([CH3:40])[CH2:34][CH2:33][N:35]([CH3:38])[CH3:36])=[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]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 131712684Benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate

Product 1

HCID 13389336HCID 13389336, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzyl 6-(1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (46 mg) N-methyl-N-(2-dimethylaminoethyl)amine (10.2 mg), and triethylamine (28 μl) in anhydrous DMF (0.5 ml) is stirred at room temperature for 4 hrs. The mixture is diluted with ethyl acetate (10 ml) washed with H2O (5×2 ml) and brine, dried with MgSO4, filtered and evaporated in vacuo to provide benzyl 6-(1-hydroxyethyl)-3-[N-methyl-N-(2-dimethylaminoethyl)amino]-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. washwashed with H2O (5×2 ml) and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-83f901b4760b4f36835a3d8c1553499c
Source dataset
uspto-grants-1984_01
Patent number
US04424230

Reaction notes

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