Nitromethane → HCID 10032156, compound

HRID 1613518Notes

Reaction equation

HRID 1613518 reaction equation
[S:1]=[C:2]1[NH:6][C:5]([C:7]2[CH:33]=[CH:32][C:10]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:28]=[CH:27][C:19]4[CH2:20][CH2:21][CH:22]([C:24]([OH:26])=[O:25])[O:23][C:18]=4[C:17]=3[CH2:29][CH2:30][CH3:31])=[C:9]([CH2:34][CH2:35][CH3:36])[C:8]=2[O:37][CH3:38])=[CH:4][S:3]1.[N+](C)([O-])=O.C1COCC1.[CH2:48](Br)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CCCCCC.C(OCC)(=O)C.C(OCC)C.O>[CH3:38][O:37][C:8]1[C:9]([CH2:34][CH2:35][CH3:36])=[C:10]([CH:32]=[CH:33][C:7]=1[C:5]1[N:6]=[C:2]([S:1][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[S:3][CH:4]=1)[O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:28]=[CH:27][C:19]2[CH2:20][CH2:21][CH:22]([C:24]([OH:26])=[O:25])[O:23][C:18]=2[C:17]=1[CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 10347709HCID 10347709, compound

Product 1

HCID 10032156HCID 10032156, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 21226206Ethyl acetate hexaneSolventHCID 21584184Diethylether waterSolvent

Procedure

The compound of Example 26 (30 mg, 53.7 μmol) was added to 1.5 ml of nitromethane, 0.5 ml of THF, and 30 ml (0.25 mmol) benzyl bromide. The mixture was allowed to react at room temperature for 1 hour. The reaction mixture was poured into ethyl ether/water, and the ether layer was washed with brine, dried over sodium sulfate, and concentrated under vacuum. Flash chromatography of the residue on silica gel using 10:1 to 7:1 hexane/ethyl acetate (1% acetic acid) gave the product (25 mg, 38.5 μmol, 72% yield). High resolution mass spectrum, m/e 648.2490 (calculated for C36H42NO6S2 (M+H), 648.2453).

Workup

  1. customto react at room temperature for 1 hour
  2. washthe ether layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a3a8091cce0143969257982f23c2471e
Source dataset
uspto-grants-1993_03
Patent number
US05192782

Reaction notes

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