Methyl 2-bromo-2-methylpropionate → HCID 86651523, compound

HRID 1912747Notes

Reaction equation

HRID 1912747 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].C(O[C:12](=[O:15])[NH:13][OH:14])(C)(C)C.Br[C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19]>CS(C)=O>[C:2]([N:13]([OH:14])[C:12]([C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19])=[O:15])([CH3:5])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 90097Methyl 2-bromo-2-methylpropionateHCID 97534tert-butyl N-hydroxycarbamateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86651523HCID 86651523, compoundYield 141.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of potassium tert-butoxide (2.78 g) in dry DMSO (40 mL), tert-butyl-N-hydroxycarbamate (3.00 g) was added. After 5 minutes methyl 2-bromoisobutyrate (2.97 g) in DMSO (50 mL) was added dropwise, maintaining the temperature below 30° C. After 0.5 hrs at room temperature the reaction was poured into ice/water (120 mL) and extracted three times with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4 and the solvent evaporated to dryness to give methyl 2-(tert-butyl-N-hydroxycarbamoyl)isobutyrate (5.04 g, 96%) which was used without purification in the next step. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 9.53 (1H, s), 3.66 (3H, s), 1.40 (9H, s), 1.33 (6H, s).

Workup

  1. temperaturemaintaining the temperature below 30° C
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent evaporated to dryness

Sources & evidence

ORD record
ord-88409e7b3b13464a9a9aa364a8b8a39a
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

Loading…