Isoamyl Nitrite → HCID 54331335, compound

HRID 851368

Reaction equation

HRID 851368 reaction equation
N[CH:2]1[C@@H:5]([CH2:6][CH:7]=[CH2:8])[N:4]([C:9](=[C:14]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:3]1=[O:17].[BrH:18].C(N(CC)CC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N(OCCC(C)C)=O>C(Cl)Cl>[Br:18][CH:2]1[C@@H:5]([CH2:6][CH:7]=[CH2:8])[N:4]([C:9](=[C:14]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:3]1=[O:17]

Participants

6

Reactant 4

HCID 8053Isoamyl NitriteHCID 521998p-Toluenesulfonic acid monohydrateHCID 2734074Triethylammonium bromideHCID 54087051HCID 54087051, compound

Product 1

HCID 54331335HCID 54331335, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl 2-[(4R)-3-amino-4-allyl-2-oxoazetidin-1-yl]-3-methyl-2-butenoate (815 mg), triethylamine hydrobromide (2.50 g) and p-toluenesulfonic acid hydrate (1.17 g) in methylene chloride (30 ml) was cooled to 0° C. and isopentyl nitrite (0.54 ml) was added. After stirring for 20 minutes at the same temperature, the mixture was concentrated and the residue was dissolved in ethyl acetate (50 ml). The solution was washed successively with 10% aqueous sodium bisulfite, water and brine, dried over magnesium sulfate and evaporated to give methyl 2-[(4R)-3-bromo-4-allyl-2-oxoazetidin-1-yl]-3-methyl-2-butenoate (840 mg) as a crude oil.

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  3. washThe solution was washed successively with 10% aqueous sodium bisulfite, water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-c105696679a9498188ae1b51bcf7cba1
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Linked notes

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