Hydrochloric Acid → [6-(5-Aminomethyl-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid

HRID 1798302Notes

Reaction equation

C([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[S:19][C:20]([CH2:23][NH2:24])=[N:21][N:22]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[OH-].[Li+].Cl>O1CCCC1.O>[NH2:24][CH2:23][C:20]1[S:19][C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:25])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:22][N:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [6-(5-aminomethyl-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.22 g, 0.6 mmol) in tetrahydrofuran (10 mL) at 0° C. was added lithium hydroxide (0.06 g, 2.42 mmol) in water (5 mL). The mixture was stirred at 0° C. for 1.5 hours then acidified to pH=2 with 2N HCl. The mixture was concentrated in vacuo and the residue purified by preparative HPLC to give [6-(5-aminomethyl-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.015 g, 7%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.37 (s, 1H), 8.58 (br. s., 3H), 7.48 (s, 1H), 7.33 (d, J=1.62 Hz, 1H), 5.56 (dd, J=9.23, 2.52 Hz, 1H), 4.43 (s, 2H), 3.10 (dd, J=15.63, 2.71 Hz, 1H), 2.34 (s, 3H), 2.18 (dd, J=15.44, 9.21 Hz, 1H); MS (ESI) m/z: 336 [M+1]+; HPLC purity: 94.12% (MaxPlot), 96.99% (220 nm).

Workup

concentrationThe mixture was concentrated in vacuo
customthe residue purified by preparative HPLC

Sources & evidence

ORD record: ord-514955ea606f4d3facf40f5885f134be
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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