Pivaloyl chloride → HCID 14460310, compound

HRID 2371901Notes

Reaction equation

HRID 2371901 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][S:12][CH:13]1[N:16]([CH2:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[C:15](=[O:31])[CH:14]1[CH:32]([O:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)=[O:36])[CH3:33].[C:48](Cl)(=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50]>O1CCCC1.C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:50][C:49]([CH3:52])([CH3:51])[C:48](=[O:53])[CH:17]([N:16]1[CH:13]([S:12][CH3:11])[CH:14]([CH:32]([O:34][C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=2)=[O:36])[CH3:33])[C:15]1=[O:31])[C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=1)=[O:19]

Participants

7

Reactant 3

HCID 62493Pivaloyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 14460309HCID 14460309, compound

Product 1

HCID 14460310HCID 14460310, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

1.1 ml of 1M lithium bis(trimethylsilyl)amide are added over the course of 5 minutes to a stirred mixture of 275 mg (0.515 mmol) of p-nitrobenzyl 2-[4-methylthio-3-(1-(p-nitrobenzyloxycarbonyloxy)-ethyl)-2-oxoazetidinyl]-acetate and 67 μl (0.55 mmol) of pivaloyl chloride in 6.7 ml of dry tetrahydrofuran at -70° C., and the reaction mixture is stirred at -70° C. for a further 30 minutes and then diluted with 40 ml of toluene and washed with 30 ml of 2N HCl, then twice with 40 ml of NaCl solution in each case. The organic phase is dried over MgSO4 and filtered, and the solvent is removed in vacuo. The residue is chromatographed over 10 g of silica gel using toluene:ethyl acetate (9:1), to give 268 g of a white, non-crystalline solid. IR spectrum in CH2Cl2 : 2930, 2850, 1775, 1760, 1720, 1610, 1535, 1350 cm-1 .

Workup

  1. washwashed with 30 ml of 2N HCl
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is removed in vacuo
  5. customThe residue is chromatographed over 10 g of silica gel
  6. customto give 268 g of a white, non-crystalline solid

Sources & evidence

ORD record
ord-1888fe3c4b2949c4be254f73730b23f9
Source dataset
uspto-grants-1992_03
Patent number
US05096899

Reaction notes

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