4-Nitrobenzyl bromoacetate → HCID 14460309, compound

HRID 2371900Notes

Reaction equation

HRID 2371900 reaction equation
C[Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Li+].[Li+].[CH3:13][S:14][CH:15]1[NH:18][C:17](=[O:19])[CH:16]1[CH:20]([O:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])[CH3:21].Br[CH2:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=1)=[O:39]>O1CCCC1.CN(C=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:13][S:14][CH:15]1[N:18]([CH2:37][C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=2)=[O:39])[C:17](=[O:19])[CH:16]1[CH:20]([O:22][C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=1)=[O:24])[CH3:21]

Participants

8

Reactant 3

HCID 70153214-Nitrobenzyl bromoacetateHCID 14460308HCID 14460308, compoundHCID 86588160Lithim bis(trimethylsilylamide)

Product 1

HCID 14460309HCID 14460309, compoundYield 48.7%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

2.2 ml of 1M solution of lithium bis(trimethylsilylamide) are added over the course of 5 minutes to a stirred mixture, at 70° C., of 680 mg (2 mmol) of 4-methylthio-3-[1-(p-nitrobenzyloxycarbonyloxy)-ethyl]-azetidin-2-one and 602 mg (2.2 mmol) of p-nitrobenzyl bromoacetate in 2 ml of dry tetrahydrofuran and 2 ml of dry DMF. The reaction mixture is stirred at -70° C. for 30 minutes, diluted with 30 ml of ethyl acetate and 70 ml of toluene and washed twice with dilute NaCl solution. The organic phase is dried over MgSO4 and filtered, and the solvent is evaporated in vacuo. The residue is chromatographed over 65 g of silica gel using toluene:ethyl acetate 4:1, to give 520 mg of a yellow oil. IR spectrum in CH2Cl2 : 2920, 2850, 1765, 1750, 1605, 1520, 1355, 1345 cm-1.

Workup

  1. washwashed twice with dilute NaCl solution
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is evaporated in vacuo
  5. customThe residue is chromatographed over 65 g of silica gel

Sources & evidence

ORD record
ord-d8efba1804cf468380c6a5c263fb7218
Source dataset
uspto-grants-1992_03
Patent number
US05096899

Reaction notes

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