Isoamyl Nitrite → HCID 54331335, compound

HRID 1719274

Reaction equation

HRID 1719274 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-d115d52a53914b2a9b8b5a416045f907
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Linked notes

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