tert-Butyl bromoacetate → HCID 86608494, compound

HRID 1432035Notes

Reaction equation

HRID 1432035 reaction equation
[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][CH:7]([CH3:10])[CH2:8][NH2:9])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[C:22]([O:26][C:27](=[O:30])[CH2:28]Br)([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C>[C:22]([O:26][C:27](=[O:30])[CH2:28][NH:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:12])[CH3:11])[CH3:10])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 58531191HCID 58531191, compound

Product 1

HCID 86608494HCID 86608494, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-(tert-Butyl-dimethyl-silanyloxy)-propylamine (6.0 g, 31.6 mmol) was dissolved in DMF (60 mL). Diisopropylethylamine (5.5 mL, 31.6 mmol) and bromo-acetic acid tert-butyl ester (3.6 g, 18.6 mmol) was added. The reaction mixture was stirred at 50° C. for 16 h. The mixture was evaporated onto silica gel and and purified by column chromatography using a gradient, starting eluting with ethyl acetate/heptane 20:80 up to ethyl acetate/heptane 80:20. The product was isolated as an oil. Yield: 4.0 g, 71%.

Workup

  1. customThe mixture was evaporated onto silica gel
  2. custompurified by column chromatography
  3. washstarting eluting with ethyl acetate/heptane 20:80 up to ethyl acetate/heptane 80:20
  4. customThe product was isolated as an oil

Sources & evidence

ORD record
ord-8aa75832e17743a8b43f5a63ffcb4b7c
Source dataset
uspto-grants-2009_11
Patent number
US07612068B2

Reaction notes

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