Hydrochloric Acid → HCID 58292673, compound

HRID 1798121Notes

Reaction equation

HRID 1798121 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[C:25]([O:24][C:22]([NH:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[CH:14]=[C:15]([CH3:16])[C:7]2[CH:6]([CH2:5][C:4]([OH:29])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=1)=[O:23])([CH3:27])([CH3:28])[CH3:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292543HCID 58292543, compound

Product 1

HCID 58292673HCID 58292673, compoundYield 108.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution [6-(3-tert-butoxycarbonylamino-propoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.445 g, 1.09 mmol) in THF (14 mL) was added a solution of LiOH (0.229 g, 5.44 mmol) in water (5 mL) at 0° C. The resulting mixture was stirred at room temperature for 3 hours then acidified to pH=2 with 6M HCl and extracted with EtOAc (3×25 mL). The organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (20% 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 (0.450 g, 80%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.08 (s, 1H), 7.00 (d, J=1.90 Hz, 1H), 6.87 (br. s., 1H), 6.81 (s, 1H), 5.41 (dd, J=9.52, 2.22 Hz, 1H), 3.93 (t, J=6.19 Hz, 2H), 3.06 (t, J=6.34 Hz, 2H), 3.00 (dd, J=15.55, 2.54 Hz, 1H), 2.23 (s, 3H), 2.03 (dd, J=15.39, 9.68 Hz, 1H), 1.80 (t, J=6.66 Hz, 2H), 1.35 (s, 9H).

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel flash column chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-267004e8c02944a1a92bf6633d4b9ec8
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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