Benzene → HCID 18924838, compound

HRID 1288825Notes

Reaction equation

HRID 1288825 reaction equation
[C:1](N1C=CN=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=O.[CH2:13]([C:15]1([CH2:44][CH3:45])[C:18](=[O:19])[N:17]([C:20]([NH:22][CH:23]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[CH2:24][CH2:25][CH3:26])=[O:21])[CH:16]1[O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=O)=[CH:37][CH:36]=1)[CH3:14].CN(C)CCN.C1C=CC=CC=1>C(Cl)Cl>[CH3:1][N:3]([CH3:4])[CH2:7][CH2:6][NH:5][C:39]([C:38]1[CH:42]=[CH:43][C:35]([O:34][CH:16]2[C:15]([CH2:44][CH3:45])([CH2:13][CH3:14])[C:18](=[O:19])[N:17]2[C:20]([NH:22][CH:23]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[CH2:24][CH2:25][CH3:26])=[O:21])=[CH:36][CH:37]=1)=[O:41]

Participants

6

Reactant 4

HCID 241BenzeneHCID 66053N,N-DimethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 21849578HCID 21849578, compound

Product 1

HCID 18924838HCID 18924838, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.104 g carbonyldiimidazole in 2 ml methylene chloride is added a solution of 0.227 g of [S-(R*,S*)]-4-((3,3-diethyl-1-((-1-(4-methylphenyl)butylamino)carbonyl)-4-oxo-2-azetidinyl)-oxy)benzoic acid in 3 ml methylene chloride. The mixture is stirred at ambient temperature for 30 minutes at which time 0.100 g of N,N-dimethylethylenediamine is added. After stirring overnight at room temperature the reaction mixture is poured into benzene (50 ml) and washed with water. The organic layer is separated, dried through sodium sulfate and concentrated in vacuo. Silica gel chromatography using 5% methanol in methylene chloride yields 0.160 g of 2-[4-[[[2-(dimethylamino)-ethyl]amino]carbonyl]phenoxy]-3,3-diethyl-N-[1-(4-methylphenyl)butyl]-4-oxo-1-azetidinecarboxamide. (Compound 73).

Workup

  1. additionis added
  2. washwashed with water
  3. customThe organic layer is separated
  4. dry with materialdried through sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-588b5a65d6c04887952112fa26535895
Source dataset
uspto-grants-1998_05
Patent number
US05747485

Reaction notes

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