Bromide ion → Methyl 2-[(tert-butoxycarbonyl)amino]pent-4-ynoate

HRID 1721166Notes

Reaction equation

HRID 1721166 reaction equation
C(O[CH:5]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]([O:8][CH3:9])=[O:7])(=O)C.[CH2:18](Br)[C:19]#[CH:20].[Br-]>CN(C=O)C.CCOC(C)=O.[Zn]>[CH3:17][C:14]([CH3:15])([O:13][C:11]([NH:10][CH:5]([CH2:20][C:19]#[CH:18])[C:6]([O:8][CH3:9])=[O:7])=[O:12])[CH3:16]

Participants

7

Reactant 3

HCID 259Bromide ionHCID 7842Propargyl bromideHCID 10922855Acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester

Product 1

HCID 10537281Methyl 2-[(tert-butoxycarbonyl)amino]pent-4-ynoate

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice cooled suspension of the product of Example 2 (4.00 g, 16.2 mmol) and zinc dust (2.63 g, 40.5 mmol) in DMF (30 mL) under nitrogen was added slowly via syringe propargyl bromide (80% w/w in toluene) (6.02 g, 40.5 mmol). The bromide was added at such a rate as to maintain the internal temperature between 20°-25° C., then stirred at that temperature for an additional 1 hour. The reaction mixture was diluted with 100 mL of EtOAc, washed successively with 0.5N HCl (200 mL), sat'd NaHCO3 (200 mL) and sat'd NaCl and then dried (MgSO4).

Workup

  1. temperatureto maintain the internal temperature between 20°-25° C.
  2. washwashed successively with 0.5N HCl (200 mL), sat'd NaHCO3 (200 mL)
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-26caa51045d747c58e987d743a3649f8
Source dataset
uspto-grants-1996_04
Patent number
US05508466

Reaction notes

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