Isobutyl chloroformate → HCID 59716773, compound

HRID 2224213Notes

Reaction equation

HRID 2224213 reaction equation
[Br:1][CH:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3](O)=[O:4].[CH3:10][N:11]1[C@@H]2CC3C=CC(OC)=C4O[C@H]5[C@@H](O)C=C[C@@H]2[C@]5(C=34)CC1.C(OC(Cl)=O)C(C)C>C1COCC1>[Br:1][CH:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([NH:11][CH3:10])=[O:4]

Participants

5

Reactant 3

HCID 62365Isobutyl chloroformateHCID 1426812-Bromo-4-methylpentanoic acidHCID 5284371Codeine

Product 1

HCID 59716773HCID 59716773, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of DL-alpha-bromoisocaproic acid in THF (4 ml) was added N-methylmorphine (0.18 ml, 1.63 mmol), followed by dropwise addition of isobutylchloroformate (0.15 ml, 1.16 mmol). A white solid precipitate was formed. After stirring at RT for 1.5 h, the white solid was filtered. Methylamine (1 ml, 2N in THF) was added to the filtrate. The reaction mixture was concentrated after 0.5 hour. The resultant crude material was diluted with ethyl acetate and washed with water. The organic layer was dried over Na2SO4 and concentrated to give the title compound, 2-bromo-N,4-dimethylpentanamide, (0.18 g, 78%) as an oil.

Workup

  1. customA white solid precipitate was formed
  2. filtrationthe white solid was filtered
  3. additionMethylamine (1 ml, 2N in THF) was added to the filtrate
  4. concentrationThe reaction mixture was concentrated after 0.5 hour
  5. additionThe resultant crude material was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7f0e9848cb214d2e823a629336443f30
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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