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

HRID 1635065Notes

Reaction equation

HRID 1635065 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-methoxybenzen sulfonylamino) 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 1.0 M 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-44fe5a7ed33a445f8d455b771cb186af
Source dataset
uspto-grants-2003_01
Patent number
US06509337B1

Reaction notes

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