N-bromobutanimide → HCID 68430788, compound

HRID 1372460Notes

Reaction equation

HRID 1372460 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:24])[CH2:9][C:10]([N:12]2[C@H:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][O:14][C:13]2=[O:23])=[O:11])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[Br:34]N1C(=O)CCC1=O>ClCCl>[Br:34][C@H:9]([C@H:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:24])[C:10]([N:12]1[C@H:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:15][O:14][C:13]1=[O:23])=[O:11]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 81531DiisopropylethylamineHCID 68430783HCID 68430783, compound

Product 1

HCID 68430788HCID 68430788, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the product from Step B (2.87 g, 7.39 mmol) in dichloromethane (40 mL) was added diisopropylethylamine (1.93 mL, 11.1 mmol) and dibutylborontriflate (9.6 mL, 1M solution in dichloromethane, 9.60 mmol) at −78° C. The light yellow solution was stirred at −78° C. for 15 min, 0° C. for 1 h and recooled to −78° C. for 15 min. The above solution was transferred to a precooled suspension of N-bromosuccinimide (3.93 g, 22.2 mmol) in dichloromethane (40 mL) via cannula. The resultant mixture was stirred at −78° C. for 1 h and 0° C. for 3 h. The reaction was quenched by addition of 0.5N aqueous sodium bisulfite solution. The organic phase was separated and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic layers were washed with saturated aqueous brine and concentrated in vacuo. Purification by flash chromatography (silica gel, 83:17 hexanes/ethyl acetate) afforded the desired product.

Workup

  1. waitrecooled to −78° C. for 15 min
  2. customThe reaction was quenched by addition of 0.5N aqueous sodium bisulfite solution
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with two portions of ethyl acetate
  5. washThe combined organic layers were washed with saturated aqueous brine
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (silica gel, 83:17 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e147480fd1534853a59323059927089d
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

Loading…