HCID 58292613, compound → HCID 58292605, compound

HRID 1798191Notes

Reaction equation

HRID 1798191 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([O:10][C:11]2[CH:12]=[C:13]([CH3:27])[C:14]3[CH:18]([CH2:19][C:20]([O:22]CC)=[O:21])[O:17][B:16]([OH:25])[C:15]=3[CH:26]=2)[CH:5]=1)(=[NH:3])[NH2:2]>[OH-].[Na+]>[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([O:10][C:11]2[CH:12]=[C:13]([CH3:27])[C:14]3[CH:18]([CH2:19][C:20]([OH:22])=[O:21])[O:17][B:16]([OH:25])[C:15]=3[CH:26]=2)[CH:5]=1)(=[NH:2])[NH2:3]

Participants

3

Reactant 1

HCID 58292613HCID 58292613, compound

Product 1

HCID 58292605HCID 58292605, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The crude ethyl 2-(6-(4-carbamimidoylpyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate was treated with aqueous NaOH solution (500 mg in 20 mL water). After stirring at room temperature for two hours, the reaction mixture was evaporated, acidified with 1N HCl to pH 3 and then concentrated. HPLC purification gave desired product as white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.4 (b, 1H), 9.54 (m, 3H), 9.20 (b, 1H), 8.38 (d, J=4.8 Hz, 1H), 7.45 (m, 2H), 7.22 (d, J=4.8 Hz, 1H), 7.05 (d, J=2 Hz, 1H), 5.52 (dd, J=9.6, 2.4 Hz, 1H), 3.09 (dd, J=15.6, 2.4 Hz, 1H), 2.30 (s, 3H), 2.13 (dd, J=15.6, 9.6 Hz, 1H). MS (ESI) m/z=42 [M+H]+.

Workup

  1. customthe reaction mixture was evaporated
  2. concentrationconcentrated
  3. customHPLC purification

Sources & evidence

ORD record
ord-a8b4c920ca5645fd8125c2ad176fc6f9
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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