Dimethylformamide → HCID 58292543, compound

HRID 1798120Notes

Reaction equation

HRID 1798120 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:16])[CH:14]=[CH:15][C:7]1=2)[CH3:2].[H-].[Na+].[C:20]([O:24][C:25](=[O:31])[NH:26][CH2:27][CH2:28][CH2:29]Br)([CH3:23])([CH3:22])[CH3:21].[CH3:32]N(C=O)C>>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:16][CH2:29][CH2:28][CH2:27][NH:26][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:31])[CH:14]=[C:15]([CH3:32])[C:7]1=2)[CH3:2]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 59525403HCID 59525403, compound

Product 1

HCID 58292543HCID 58292543, compoundYield 40%

Conditions

Temperature
0 °C

Procedure

To a solution of (1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.500 g, 1.99 mmol) in DMF (20 mL) was added NaH (0.176 g, 4.40 mmol) and the mixture was stirred at 0° C. for 45 minutes. A solution of (3-bromo-propyl)-carbamic acid tert-butyl ester (1.04 g, 4.38 mmol) in DMF (5 mL) was added and the mixture was stirred at room temperature for 18 hours. The reaction mixture was quenched with H2O and extracted with EtOAc (3×50 mL). The organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (33-66% EtOAc/Hexane) to give [6-(3-tert-butoxycarbonylamino-propoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.325 g, 40%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.00 (s, 1H), 6.87 (br. s., 1H), 6.81 (s, 1H), 5.43 (d, J=7.42 Hz, 1H), 3.97-4.10 (m, 2H), 3.93 (t, J=6.06 Hz, 2H), 2.99-3.08 (m, 3H), 2.23 (s, 3H), 2.14-2.22 (m, 1H), 1.72-1.85 (m, 2H), 1.35 (s, 9H), 1.08-1.19 (m, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. customThe reaction mixture was quenched with H2O
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash column chromatography (33-66% EtOAc/Hexane)

Sources & evidence

ORD record
ord-e942f55c3c3548c093764b7601bb73d0
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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