Sodium hydride → HCID 58292874, compound

HRID 1798113Notes

Reaction equation

HRID 1798113 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2].[H-].[Na+].Br[CH2:22][C:23]([NH2:25])=[O:24]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][CH2:22][C:23](=[O:24])[NH2:25])[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292874HCID 58292874, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.2 g, 0.8 mmol) in anhydrous DMF (3 mL) was added sodium hydride (0.08 g, 2.0 mmol). After stirring for 15 minutes 2-bromo-acetamide (0.166 g, 1.2 mmol) was added and the resulting mixture stirred at room temperature for 18 hours then quenched with crushed ice. The pH was adjusted to 3 with 6M HCl and the mixture extracted with EtOAc. The organic extracts were washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (0-5% MeOH in DCM) to give 6-carbamoylmethoxy-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.13 g, 53%). 1H NMR 400 MHz (DMSO-d6) δ 9.17 (s, 1H), 7.47 (s, 1H), 7.36 (s, 1H), 7.02 (s, 1H), 6.89 (s, 1H), 5.45 (m, 1H), 4.40 (s, 2H), 4.09-4.02 (m, 2H), 3.10 (dd, J=15.2, 2.4 Hz, 1H), 2.26-2.17 (m, 4H), 1.17-1.04 (m, 3H).

Workup

  1. additionwas added
  2. customthen quenched with crushed ice
  3. extractionthe mixture extracted with EtOAc
  4. washThe organic extracts were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash column chromatography (0-5% MeOH in DCM)
  9. customto give 6-carbamoylmethoxy-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.13 g, 53%)

Sources & evidence

ORD record
ord-9753c4e1a0ee423fbcaa0081e5fe2faf
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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