tert-Butyl bromoacetate → HCID 53823464, compound

HRID 343621Notes

Reaction equation

HRID 343621 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, 1.0M solution in tetrahydrofuran). 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-3cb89bb54e1d4fd88c26e1af79ba4876
Source dataset
uspto-grants-1999_01
Patent number
US05861510

Reaction notes

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