Bromide ion → Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

HRID 1721167Notes

Reaction equation

HRID 1721167 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)[CH:19]=[CH2:20].[Br-]>CN(C=O)C.[Zn]>[CH3:9][O:8][C:6](=[O:7])[CH:5]([NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:20][CH:19]=[CH2:18]

Participants

6

Reactant 3

HCID 259Bromide ionHCID 7841Allyl bromideHCID 10922855Acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester

Product 1

HCID 10857232Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoateYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

To an ice cooled suspension of the product of Example 2 (0.525 mg, 2.12 mmol) and zinc dust (278 mg, 4.25 mmol) in DMF (4 mL) under nitrogen was added slowly via syringe neat allyl bromide (514 mg, 4.25 mmol). The bromide was added at such a rate as to maintain the internal temperature between 20 and 25° C., then stirred at that temperature for an additional 1 hour. Extractive workup and silica gel chromatography as described in Example 3 afforded 486 mg (100%) of product as a colorless oil.

Workup

  1. temperatureto maintain the internal temperature between 20 and 25° C.

Sources & evidence

ORD record
ord-09f602e4b00c4444a78b832120fb36a6
Source dataset
uspto-grants-1996_04
Patent number
US05508466

Reaction notes

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