Lithium Hexamethyldisilazide → HCID 14460309, compound

HRID 1031048Notes

Reaction equation

HRID 1031048 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][S:12][CH:13]1[NH:16][C:15](=[O:17])[CH:14]1[CH:18]([O:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:22])[CH3:19].Br[CH2:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=1)=[O:37]>O1CCCC1.CN(C=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:11][S:12][CH:13]1[N:16]([CH2:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=2)=[O:37])[C:15](=[O:17])[CH:14]1[CH:18]([O:20][C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=1)=[O:22])[CH3:19]

Participants

9

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 70153214-Nitrobenzyl bromoacetateHCID 14460308HCID 14460308, compound

Product 1

HCID 14460309HCID 14460309, compound

Reagents, catalysts & solvents 5

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

2.2 ml of a 1 M solution of lithium bis-(trimethylsilyl)amide are added with stirring at -70° C. in the course of 5 minutes to a mixture of 680 g (2mmol) 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. during the course of 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 on 65 g of silica gel using toluene/ethyl acetate 4:1, 520 mg of a yellow oil being obtained. 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 on 65 g of silica gel
  6. custombeing obtained

Sources & evidence

ORD record
ord-9de78e9bab8844e087588ae054cd035b
Source dataset
uspto-grants-1992_04
Patent number
US05108747

Reaction notes

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