Hydrochloric Acid → HCID 58292548, compound

HRID 1798122Notes

Reaction equation

HRID 1798122 reaction equation
Cl.CO.C(OC([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH3:30])[C:19]2[CH:23]([CH2:24][C:25]([OH:27])=[O:26])[O:22][B:21]([OH:28])[C:20]=2[CH:29]=1)=O)(C)(C)C.[Li+].[OH-]>O>[NH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH3:30])[C:19]2[CH:23]([CH2:24][C:25]([OH:27])=[O:26])[O:22][B:21]([OH:28])[C:20]=2[CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 3939Lithium HydroxideHCID 58292673HCID 58292673, compound

Product 1

HCID 58292548HCID 58292548, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.25M HCl in methanol (5 mL, 6.0 mmol) was added to [6-(3-tert-butoxycarbonylamino-propoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.345 g, 0.80 mmol) at room temperature and stirred for 18 hours then concentrated in vacuo. The residue was dissolved in THF (14 mL) and a solution of LiOH (0.229 g, 5.44 mmol) in water (5 mL) at 0° C. was added. 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 preparative HPLC to give [6-(3-amino-propoxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid as a white solid (0.035 g, 14%). 1H NMR (400 MHz, methanol-d4) δ ppm 6.93 (br. s., 1H), 6.79 (br. s., 1H), 5.49 (d, J=5.86 Hz, 1H), 4.10 (t, J=5.47 Hz, 2H), 3.15 (t, J=7.03 Hz, 2H), 2.97 (d, J=14.85 Hz, 1H), 2.27 (s, 3H), 2.03-2.21 (m, 3H). MS (ESI) m/z: 280 [M+1]+. HPLC purity: 96.23% (Maxplot), 95.78% (220 nm).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in THF (14 mL)
  3. stirringThe resulting mixture was stirred at room temperature for 3 hours
  4. extractionextracted with EtOAc (3×25 mL)
  5. washThe organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-29d31052fc7a4d41b18549b8e30e5096
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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