1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-5-methyl-1,3-oxazole-4-carboxylate

HRID 43626Notes

Reaction equation

HRID 43626 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][CH:20]([CH3:27])[CH:21]([C:23]([O:25][CH3:26])=[O:24])[N:22]=2)=[CH:14][C:13]=1[CH3:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrCC(Cl)(Cl)Cl.C1CCN2C(=NCCC2)CC1>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20]([CH3:27])=[C:21]([C:23]([O:25][CH3:26])=[O:24])[N:22]=2)=[CH:14][C:13]=1[CH3:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 182782Ethane, bromotrichloro-HCID 67548562Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate

Product 1

HCID 67548521Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-5-methyl-1,3-oxazole-4-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate obtained in Example (108c) (4.4 g, 11.5 mmol) in dichloromethane (50 mL) was cooled to 0° C., and bromotrichloroethane (3.20 g, 16.1 mmol) and DBU (2.45 g, 16.1 mmol) were added. The mixture was stirred at the same temperature for three hours, washed with a 1 N aqueous hydrochloric acid solution and brine, and dried over magnesium sulfate. Following concentration, the resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/2, 2/1) to obtain 1.75 g of the title compound as a colorless solid (40%).

Workup

  1. washwashed with a 1 N aqueous hydrochloric acid solution and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentration
  4. customthe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/2, 2/1)

Sources & evidence

ORD record
ord-5377306d8e8a4ba3ab28425e0c23d720
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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