Pivaloyl chloride → HCID 14460310, compound

HRID 1031049Notes

Reaction equation

HRID 1031049 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.Cl.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

8

Reactant 3

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

Product 1

HCID 14460310HCID 14460310, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

1.1 ml of 1 M lithium bis(trimethylsilyl)-amide are added at -70° C. with stirring in the course of 5 minutes to a 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 and the reaction mixture is stirred at -70° C. during the course of a further 30 minutes and then diluted with 40 ml of toluene and with 30 ml of 2 N HCl, then washed twice with 40 ml each of NaCl solution. The organic phase is dried over MgSO4 and filtered, and the solvent is removed in vacuo. The residue is chromatographed on 10 g of silica gel using toluene/ethyl acetate (9:1), 268 mg of a white non-crystalline solid being obtained. IR spectrum in CH2Cl2 : 2930, 2850, 1775, 1760, 1720, 1610, 1535, 1350 cm-1 .

Workup

  1. washwashed twice with 40 ml each of NaCl solution
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is removed in vacuo
  5. customThe residue is chromatographed on 10 g of silica gel
  6. customobtained

Sources & evidence

ORD record
ord-79d5bc37ab3a4edda9d3988a230053e4
Source dataset
uspto-grants-1992_04
Patent number
US05108747

Reaction notes

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