Sodium hydride → HCID 10114634, compound

HRID 1815218Notes

Reaction equation

HRID 1815218 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:30])=[CH:5][C@@H:6]1[N:20]2[C:21]([C@H:23]3[N:27]([C:28](=[O:29])[C@@H:19]2[CH2:18][C:8]2[C:9]4[CH:10]=[CH:11][C:12]([O:16][CH3:17])=[CH:13][C:14]=4[NH:15][C:7]1=2)[CH2:26][CH2:25][CH2:24]3)=[O:22].[CH3:31][C:32]([CH3:36])=[CH:33][CH2:34]Br.[Cl-].[NH4+]>ClCCl>[CH3:17][O:16][C:12]1[CH:13]=[C:14]2[C:9]([C:8]3[CH2:18][C@H:19]4[C:28](=[O:29])[N:27]5[CH2:26][CH2:25][CH2:24][C@H:23]5[C:21](=[O:22])[N:20]4[C@@H:6]([CH:5]=[C:4]([CH3:30])[CH3:3])[C:7]=3[N:15]2[CH2:34][CH:33]=[C:32]([CH3:36])[CH3:31])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 700922-Butene, 1-bromo-3-methyl-HCID 403923Fumitremorgin C

Product 1

HCID 10114634HCID 10114634, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of sodium hydride (0.12 mol) in dry dichloromethane (0.1 ml) was added a solution of fumitremorgin C (0.05 mmol) in dichloromethane (0.5 ml) under an atmosphere of nitrogen at room temperature. Upon stirring for forty-five minutes, 3,3-dimethyl allyl bromide (0.11 mmol) was added and the reaction mixture stirred under nitrogen for two hours. Saturated aqueous solution of ammonium chloride was then added, and the alkylation product was extracted with ethyl acetate and purified by HPLC on a C18 column using methanol/water as mobile phase. MS and 1H NMR spectra were consistent with the desired product.

Workup

  1. stirringthe reaction mixture stirred under nitrogen for two hours
  2. extractionthe alkylation product was extracted with ethyl acetate
  3. custompurified by HPLC on a C18 column

Sources & evidence

ORD record
ord-efc150f26a8144deb6b0fbe1f1020dce
Source dataset
uspto-grants-2005_04
Patent number
US06878737B2

Reaction notes

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