Triphenylphosphine → HCID 18512211, compound

HRID 1370854Notes

Reaction equation

HRID 1370854 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][CH2:37][CH2:38]O)[CH:30]=2)=[CH:24][CH:23]=1)[C:9]1[C:10]([CH3:20])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:59]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH2:36][CH2:37][CH2:38][Br:59])[CH:30]=2)=[CH:24][CH:23]=1)[C:9]1[C:10]([CH3:20])=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 18512094HCID 18512094, compound

Product 1

HCID 18512211HCID 18512211, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude product from Example 72C and triphenylphosphine (0.730 g, 2.78 mmoles) in anhydrous DMF (5 mL) at 0° C. were treated with N-bromosuccinimide (0.396 g, 2.24 mmoles). Reaction mixed at 0° C. for 30 minutes. Reaction diluted with ethyl acetate, washed with H2O (2×), brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 30% ethyl acetate:hexanes) to provide the title compound (0.214 g, 63%). MS (ESI+) m/z 609 (M+H)+.

Workup

  1. customReaction
  2. additionmixed at 0° C. for 30 minutes
  3. customReaction
  4. washwashed with H2O (2×), brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (silica gel, 30% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-1c78ad16f1144614a26cb83bb0e8a41a
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

Loading…