Hydrochloric Acid → HCID 66693554, compound

HRID 2368000Notes

Reaction equation

HRID 2368000 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:18]2[B:19]([OH:26])[O:20][CH:21]([CH2:22][N+:23]([O-:25])=[O:24])[C:17]=2[CH:16]=[C:15]([Cl:27])[CH:14]=1)C1C=CC=CC=1.Cl.[H][H]>CO.[OH-].[OH-].[Pd+2]>[Cl:27][C:15]1[CH:14]=[C:13]([O:12][CH2:11][CH2:10][CH2:9][OH:8])[C:18]2[B:19]([OH:26])[O:20][CH:21]([CH2:22][N+:23]([O-:25])=[O:24])[C:17]=2[CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66693123HCID 66693123, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66693554HCID 66693554, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

7-(3-Benzyloxy-propoxy)-5-chloro-3-nitromethyl-3H-benzo[c][1,2]oxaborol-1-ol (0.3 g, 0.91 mmol) in MeOH (30 mL) was added conc HCl (1 mL) and Pd(OH)2 (10% w/w on carbon, 0.2 g) and the reaction vessel was pressurized to 40 psi with hydrogen for 30 minutes at room temperature. The mixture was filtered through a pad of Celite® and washed with EtOAc. The filtrate was concentrated in vacuo and the product was purified by prep. HPLC(C18 column, using acetonitrile and 0.1% AcOH/water solution gradient) provided the title compound (80 mg, 33%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.19 (s, 1H), 7.22 (s, 1H), 6.97 (s, 1H), 5.71 (dd, J=8.9, 2.3 Hz, 1H), 5.32 (dd, J=13.2, 2.7 Hz, 1H), 4.64 (dd, J=13.6, 8.9 Hz, 1H), 4.53 (t, J=4.8 Hz, 1H), 4.12 (t, J=6.0 Hz, 2H), 3.57 (q, J=5.5 Hz, 2H), 1.86 (t, J=6.2 Hz, 2H).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe product was purified by prep

Sources & evidence

ORD record
ord-c3c856c903114057974c5ce8a8654fe1
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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