Benzyl Bromide → HCID 101593917, compound

HRID 850645Notes

Reaction equation

HRID 850645 reaction equation
[CH3:1][CH2:2][C@:3]1([C@@H:31]2[O:35][C@@H:34]([C@H:36]3[O:41][C@@:40]([OH:44])([CH2:42][OH:43])[C@H:39]([CH3:45])[CH2:38][C@@H:37]3[CH3:46])[CH2:33][C@@H:32]2[CH3:47])[O:7][C@@H:6]([C@@:8]2([CH3:30])[O:12][C@:11]3([O:17][C@H:16]([C@H:18]([C@@H:20]([O:26][CH3:27])[C@@H:21]([C:23]([O-:25])=[O:24])[CH3:22])[CH3:19])[C@H:15]([CH3:28])[C@@H:14]([OH:29])[CH2:13]3)[CH2:10][CH2:9]2)[CH2:5][CH2:4]1.[Na+].N12CCC(CC1)CN2.[CH2:57](Br)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>C(#N)C>[CH3:1][CH2:2][C@:3]1([C@@H:31]2[O:35][C@@H:34]([C@H:36]3[O:41][C@@:40]([OH:44])([CH2:42][OH:43])[C@H:39]([CH3:45])[CH2:38][C@@H:37]3[CH3:46])[CH2:33][C@@H:32]2[CH3:47])[O:7][C@@H:6]([C@@:8]2([CH3:30])[O:12][C@:11]3([O:17][C@H:16]([C@H:18]([C@@H:20]([O:26][CH3:27])[C@@H:21]([C:23]([O:25][CH2:57][C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)=[O:24])[CH3:22])[CH3:19])[C@H:15]([CH3:28])[C@@H:14]([OH:29])[CH2:13]3)[CH2:10][CH2:9]2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 7498Benzyl Bromide2×HCID 136165Diazabicyclo(2.2.2)octaneHCID 23667299Monensin sodium

Product 1

HCID 101593917HCID 101593917, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Monensin sodium salt (1.0 g, 1.4 mmol) in acetonitrile (20 ml) was treated with diazabicyclo [2.2.2] octane (0.3 g, 2.7 mmol) followed by benzyl bromide (2 g, 11.7 mmol) and cryptand [2.2.2]. The reaction mixture was stirred at room temperature with exclusion of light for 14 days. After 10 days an additional quantity of benzyl bromide (2 g, 11.7 mmol) was added. The solvent was evaporated and the crude product redissolved in dichloromethane, washed with deionized water and dried over magnesium sulfate. The crude product was chromatographed on silica gel eluting with hexane-ethyl acetate gradient. Excess benzyl bromide eluted from the column first followed by benzylmonensin which was isolated as a colorless oil after removal of the solvent (280 mg, 26%), (MS, positive ion ESI showed 783 peak; calc. for sodiated product 783). This compound has been reported previously (Tsukube J. Org. Chem. 56, 875, 1991).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude product redissolved in dichloromethane
  3. washwashed with deionized water
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product was chromatographed on silica gel eluting with hexane-ethyl acetate gradient
  6. washExcess benzyl bromide eluted from the column
  7. customwas isolated as a colorless oil
  8. customafter removal of the solvent (280 mg, 26%), (MS, positive ion ESI showed 783 peak; calc. for sodiated product 783)

Sources & evidence

ORD record
ord-7c9a8bd922284796a27bde6e1850f664
Source dataset
uspto-grants-2000_01
Patent number
US06017950

Reaction notes

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