2-Butene, 1-bromo-3-methyl- → HCID 53702490, compound

HRID 343623Notes

Reaction equation

HRID 343623 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35]>O1CCCC1.CN(C)C=O>[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 700922-Butene, 1-bromo-3-methyl-HCID 2724254Sodium bis(trimethylsilyl)amideHCID 53813733HCID 53813733, compound

Product 1

HCID 53702490HCID 53702490, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of (4-methoxybenzenesulfonylamino) acetic acid t-butyl ester (3.0 grams, 10 mmol) in tetrahydrofuran-dimethylformamide (mL, ca. 3:1) at 0° C. is added sodium bis(trimethylsilyl)amide (10.0 mL, 1.0M solution in tetrahydrofuran). After 10 minutes, 4-bromo-2-methyl-2-butene (1.27 μL, 11.0 mmol) is added. The mixture is warmed to room temperature, stirred for 1 hour and quenched with saturated ammonium chloride solution. The mixture is extracted with ethyl acetate and the combined extracts are dried (sodium sulfate), filtered and concentrated. The crude product is purified by silica gel chromatography (elution with 1:1 ethyl acetate-hexanes) to provide [(4-methoxybenzenesulfonyl)-(3-methyl-but-2-enyl)-amino]-acetic acid t-butyl ester.

Workup

  1. customquenched with saturated ammonium chloride solution
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe combined extracts are dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel chromatography (elution with 1:1 ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-55a57665c0664e04a1b354a892ea9349
Source dataset
uspto-grants-1999_01
Patent number
US05861510

Reaction notes

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