Hydrochloric Acid → HCID 178428838, compound

HRID 1798186Notes

Reaction equation

HRID 1798186 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][C:13]3[CH:18]=[C:17]([C:19](=[NH:22])[NH:20][OH:21])[CH:16]=[CH:15][N:14]=3)[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:23][C:24]([O:26]CC)=[O:25])[O:3]1.Cl>[OH-].[Na+]>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][C:13]3[CH:18]=[C:17]([C:19](=[NH:22])[NH:20][OH:21])[CH:16]=[CH:15][N:14]=3)[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:23][C:24]([OH:26])=[O:25])[O:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178470804HCID 178470804, compound

Product 1

HCID 178428838HCID 178428838, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-(ethyl 2-(1-hydroxy-6-(4-(N-hydroxycarbamimidoyl)pyridin-2-yloxy)-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (150 mg) was treated with NaOH solution (200 mg in 10 ml water) for one hour at room temperature. The reaction mixture was acidified to pH 5 with 6 N HCl and then concentrated. HPLC purification gave product as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.5 (b, 1H), 9.20 (b, 1H), 8.23 (d, J=5.2 Hz, 1H), 7.04 (dd, J=5.2, 1.2 Hz, 1H), 7.34 (s, 1H), 7.23 (s, 1H), 7.06 (d, J=1.6 Hz, 1H), 5.53 (dd, J=9.6, 2.4 Hz, 1H), 3.10 (dd, J=15.6, 2.4 Hz, 1H), 2.50 (s, 3H), 2.28 (dd, J=10, 9.6 Hz, 1H). 3 protons assumed to be exchanged with solvents. MS (ESI) m/z=358 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customHPLC purification
  3. customgave product as a white solid

Sources & evidence

ORD record
ord-97f40b6174ce4cdb99c9645945f57ca2
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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