Lithium Hydroxide → 2-(6-(5-Carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

HRID 1798315Notes

Reaction equation

HRID 1798315 reaction equation
[C:1]([C:4]1[S:8][C:7]([O:9][C:10]2[CH:11]=[C:12]([CH3:26])[C:13]3[CH:17]([CH2:18][C:19]([O:21]CC)=[O:20])[O:16][B:15]([OH:24])[C:14]=3[CH:25]=2)=[N:6][N:5]=1)(=[O:3])[NH2:2].[Li+].[OH-]>C1COCC1.O>[C:1]([C:4]1[S:8][C:7]([O:9][C:10]2[CH:11]=[C:12]([CH3:26])[C:13]3[CH:17]([CH2:18][C:19]([OH:21])=[O:20])[O:16][B:15]([OH:24])[C:14]=3[CH:25]=2)=[N:6][N:5]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58292581Ethyl 2-(6-(5-carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 582927952-(6-(5-Carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution ethyl 2-(6-(5-carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.448 mmol) in THF (3 mL) was added a solution of LiOH (2.24 mmol) in water (3 mL) at 0° C. The resulting mixture was stirred at room temperature for 3 hours then concentrated in vacuo. The residue was purified by preparative HPLC then lyophilized to give 2-(6-(5-carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid as an off white solid (17%). 1H NMR (400 MHz, DMSO-d6) δ 12.32 (s, 1H), 9.31 (s, 1H), 8.44 (s, 1H), 8.07 (s, 1H), 7.48 (s, 1H), 7.36 (s, 1H), 5.54 (dd, 1H), 3.07 (dd, 1H), 2.32 (s, 3H), 2.18 (dd, 1H). MS (ESI) m/z: 348.1 [M−1]−.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6a2c79571a714cb3bd79ad7b0eb00f1d
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…