Lithium Hydroxide → HCID 178428913, compound

HRID 1798319Notes

Reaction equation

HRID 1798319 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])=[N: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.[Li+].[OH-]>C1COCC1.CO>[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])=[N: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

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178470807HCID 178470807, compound

Product 1

HCID 178428913HCID 178428913, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude ethyl 2-(1-hydroxy-6-(5-(N-hydroxycarbamimidoyl)-1,3,4-thiadiazol-2-yloxy)-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate was dissolved in a mixture of THF and MeOH (1:1, 5 ml) and then treated with aqueous LiOH solution (200 mg in 5 mL water). After stirring at room temperature for one hour, 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), 10.3 (b, 1H), 9.20 (b, 1H), 7.41 (d, J=2Hz, 1H), 7.28 (d, J=1.6 Hz, 1H), 5.48 (dd, J=9.2, 2 Hz, 1H), 4.07 (b, 2H), 3.00 (dd, J=15.6, 2.4 Hz, 1H), 2.27 (s, 3H), 2.10 (dd, J=15.6, 9.2 Hz, 1H). MS (ESI) m/z=363 [M−H]+.

Workup

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

Sources & evidence

ORD record
ord-7808fbde7de74b78999f56f4a3dea571
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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