Sodium Hydroxide → HCID 178428888, compound

HRID 1798283Notes

Reaction equation

HRID 1798283 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][C:13]3[S:14][C:15]([C:18](=[NH:21])[NH:19][OH:20])=[CH:16][N:17]=3)[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:22][C:23]([O:25]CC)=[O:24])[O:3]1.[OH-].[Na+]>CO.C1COCC1>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][C:13]3[S:14][C:15]([C:18](=[NH:21])[NH:19][OH:20])=[CH:16][N:17]=3)[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:22][C:23]([OH:25])=[O:24])[O:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178470806HCID 178470806, compound

Product 1

HCID 178428888HCID 178428888, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The crude ethyl 2-(1-hydroxy-6-(5-(N-hydroxycarbamimidoyl)thiazol-2-yloxy)-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate in MeOH/THF (10 mL, 1:1) was added aqueous NaOH solution (200 mg in 3 mL water). After stirring at room temperature for two hours, the reaction mixture was evaporated, acidified with 1N HCl to pH 5 and then concentrated. HPLC purification gave desired product as white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.2 (b, 2H), 9.20 (b, 1H), 7.70 (s, 1H), 7.37 (d, J=2 Hz, 1H), 7.22 (d, J=1.6 Hz, 1H), 5.48 (dd, J=9.2, 2 Hz, 1H), 3.02 (dd, J=15.6, 2.4 Hz, 1H), 2.26 (s, 3H), 2.28 (dd, J=15.6, 9.6 Hz, 1H). 2 protons assumed to be exchanged with solvents. MS (ESI) m/z=364 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-a156929b33da4585bd755f717ce7c0fe
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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