Carbon tetrabromide → HCID 67243714, compound

HRID 2425450Notes

Reaction equation

HRID 2425450 reaction equation
O[CH2:2][CH2:3][O:4][CH2:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1)=[O:7].C(Br)(Br)(Br)[Br:22]>ClCCl>[Br:22][CH2:2][CH2:3][O:4][CH2:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1)=[O:7]

Participants

4

Reactant 2

HCID 11205Carbon tetrabromideHCID 67243255HCID 67243255, compound

Product 1

HCID 67243714HCID 67243714, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-3-[2-(2-hydroxyethoxy)acetyl]amino-1-(tert-butoxycarbonyl)pyrrolidine (4 g) prepared in Step B and carbon tetrabromide (5.52 g, Wako Pure Chemical Industries) in dichloromethane (52 ml) was added with PS (polystyrene)-triphenylphosphine (7.86 g, Aldrich) at 0° C., and the mixture was stirred at the same temperature for 3.5 hours. The insoluble solids were removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate) to obtain the title compound (3.7 g).

Workup

  1. customThe insoluble solids were removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-88d6d0664089465e82ae0be4dba1f4bf
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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