tert-Butyl bromoacetate → HCID 53823464, compound

HRID 1635062Notes

Reaction equation

HRID 1635062 reaction equation
[OH:1][CH:2](/[CH:16]=[CH:17]/[CH3:18])[CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:29]([O:33][C:34](=[O:37])[CH2:35]Br)([CH3:32])([CH3:31])[CH3:30]>O1CCCC1.CN(C)C=O>[C:29]([O:33][C:34](=[O:37])[CH2:35][N:4]([CH2:3][CH:2]([OH:1])[CH:16]=[CH:17][CH3:18])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18675474HCID 18675474, compound

Product 1

HCID 53823464HCID 53823464, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of (±)-(E)-N-(2-hydroxy-pent-3-enyl)-4-methoxybenzenesulfonamide (1.2 grams, 4.42 mmol) in tetrahydrofuran-dimethylformamide (10 mL, ca. 3:1) at 0° C. is added sodium bis(trimethylsilyl)amide (4.9 mL, 1.0 M solution in torahydrofuran). After 10 minutes, t-butylbromoacetate (786 mL, 4.83 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 [(2-hydroxy-pent-3-enyl)-(4-methoxybenzenesulfonyl)-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-1ee0577740f848f49127eebd6c460db1
Source dataset
uspto-grants-2003_01
Patent number
US06509337B1

Reaction notes

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