Benzyl Bromide → HCID 11467790, compound

HRID 1437594Notes

Reaction equation

HRID 1437594 reaction equation
[N+:1]([O:4][CH:5]([CH2:33][O:34][N+:35]([O-:37])=[O:36])[CH2:6][O:7][C:8]([O:10][CH2:11]/[C:12](/[C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[C:13](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)\[C:14]([OH:16])=[O:15])=[O:9])([O-:3])=[O:2].[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:1]([O:4][CH:5]([CH2:33][O:34][N+:35]([O-:37])=[O:36])[CH2:6][O:7][C:8]([O:10][CH2:11]/[C:12](/[C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:30])=[O:31])=[CH:27][CH:28]=1)=[C:13](/[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)\[C:14]([O:16][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:15])=[O:9])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 57941613HCID 57941613, compound

Product 1

HCID 11467790HCID 11467790, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 300 mg of (2Z)-4-({[2,3-bis(nitrooxy)propoxy]carbonyl}oxy)-3-[4-(methylsulfonyl)phenyl]-2-phenylbut-2-enoic acid in 5 mL of DMF was added 69 μL benzyl bromide followed by 81 mg of potassium carbonate (325 mesh). The resulting mixture was stirred at rt for 30 min. The reaction was then quenched with saturated solution of NH4Cl and extracted with Et2O/hexanes (½, 2 times). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give a pale yellow residue. Flash chromatography of the crude material over silica gel (10-70% EtOAc/hexane) afforded 250 mg of the title compound as a white solid. 1H NMR (500 μL, acetone-d6): δ 7.80 (d, 2H), 7.48 (d, 2H), 7.42-7.35 (m, 5H), 7.21-7.18 (m, 3H), 7.13-7.10 (m, 2H), 5.77-5.73 (m, 1H), 5.36 (s, 2H), 5.33 (s, 2H), 5.04 (dd, 1H), 4.84 (dd, 1H), 4.64 (dd, 1H), 4.48 (dd, 1H), 3.08 (s, 3H).

Workup

  1. customThe reaction was then quenched with saturated solution of NH4Cl
  2. extractionextracted with Et2O/hexanes (½, 2 times)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a pale yellow residue

Sources & evidence

ORD record
ord-09c5952b44554868b364e815bcbf6217
Source dataset
uspto-grants-2009_11
Patent number
US07622501B2

Reaction notes

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