Acetone cardice → HCID 86738831, compound

HRID 355225Notes

Reaction equation

HRID 355225 reaction equation
[C:1](=[O:3])=[O:2].CC(C)=O.[Si]([N:15]1[C@@H:18]([S:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:17]([CH2:39]O)[C:16]1=[O:41])(C(C)(C)C)(C)C.[Li]CCCC>O1CCCC1>[CH:1]([O:3][CH2:39][C@H:17]1[C@H:18]([S:19][C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[NH:15][C:16]1=[O:41])=[O:2]

Participants

5

Reactant 3

HCID 18522661Acetone cardiceHCID 70530323HCID 70530323, compoundHCID 178418339Butyllithium

Product 1

HCID 86738831HCID 86738831, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (dry ice-acetone bath, -78° C.) solution of trans 1-(t-butyldimethylsilyl)-3-hydroxymethyl-4-tritylthio-2-azetidinone (4.89 g, 10 mmol) in tetrahydrofuran (15 ml) was added dropwise 1.6 M n-BuLi (8.2 mmol). The red solution was stirred in a cold bath for 25 min and then treated dropwise with a solution of paranitrobenzylchloroformate (2.6 g, 12 mmol). Stirring was continued for 2 h. The reaction mixture was partitioned between ammonium chloride and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate (2×10 ml). The organic layers were combined and washed with brine, dried (MgSO4), and evaporated in vacuo. The residual oil was chromatographed on a silica gel column (70 g). Elution with benzene gave the title compound 4.0 g (60%) as an amorphous solid. ir νmax (CDCl3) 1750, 1610 cm-1 1 Hmr (CDCl3) δ: 8.40 (2H, d, J=9), 7.45 (17H, m), 5.22 (2H, s, benzyl), 4.4 (1H, d, J=1.5, H-4), 4.05 (1H, dd, J=14, J=4.5, H-1'), 3.28 (1H, m, H-3), 3.18 (1H, dd, J=14, J=4, H=1'), 0.95 (9H, s, t-Bu) and 0.32 ppm (6H, s, CH3).

Workup

  1. stirringStirring
  2. waitwas continued for 2 h
  3. customThe reaction mixture was partitioned between ammonium chloride and ethyl acetate
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate (2×10 ml)
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customThe residual oil was chromatographed on a silica gel column (70 g)
  10. washElution with benzene

Sources & evidence

ORD record
ord-172f8cb784c34a3783dd5d73884c2105
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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