Triphenylphosphine → 1,1-Dimethylethyl (2S)-4-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]butanoate

HRID 591272Notes

Reaction equation

HRID 591272 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:20][CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 11054918(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

Product 1

HCID 141930431,1-Dimethylethyl (2S)-4-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]butanoateYield 41.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.00 g (18.2 mmol) tert-butyl N-(tert-butoxycarbonyl)-L-homoserinate (prepared according to J. Org. Chem. 1988, 53, 1900-1903), 3.23 g N-bromo succinimide (18.2 mmol), and 6.16 g polymer bound triphenylphosphine (loading approx. 3 mmol/g, approx. 18.5 mmol) in dichloromethane (60 mL) was stirred overnight at room temperature. All solids were removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (2.5→25% ethyl acetate in hexane) to give 2.56 g of the title compound (38% yield).

Workup

  1. customAll solids were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (2.5→25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7ae8e20f92f84cd8af7a282740be61bd
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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