Nitromethane → HCID 19981399, compound

HRID 1461163Notes

Reaction equation

HRID 1461163 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]=2OC)=[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>[C:49]1([CH2:48][S:1][C:2]2[S:3][CH:4]=[C:5]([C:7]3[CH:33]=[CH:32][C:10]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]4[CH:28]=[CH:27][C:19]5[CH2:20][CH2:21][CH:22]([C:24]([OH:26])=[O:25])[O:23][C:18]=5[C:17]=4[CH2:29][CH2:30][CH3:31])=[C:9]([CH2:34][CH2:35][CH3:36])[CH:8]=3)[N:6]=2)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

7

Reactant 4

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

Product 1

HCID 19981399HCID 19981399, 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-7d7ebde71baa4c838668c8a98df6d171
Source dataset
uspto-grants-1991_12
Patent number
US05073562

Reaction notes

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