Hydrochloric Acid → 2-(6-(5-Amino-1,3,4-thiadiazol-2-yloxy)-4-chloro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

HRID 1798305Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5]([O:7][C:8]2[CH:9]=[C:10]([Cl:24])[C:11]3[CH:15]([CH2:16][C:17]([O:19]CC)=[O:18])[O:14][B:13]([OH:22])[C:12]=3[CH:23]=2)=[N:4][N:3]=1.[Li+].[OH-].Cl>C1COCC1.O>[NH2:1][C:2]1[S:6][C:5]([O:7][C:8]2[CH:9]=[C:10]([Cl:24])[C:11]3[CH:15]([CH2:16][C:17]([OH:19])=[O:18])[O:14][B:13]([OH:22])[C:12]=3[CH:23]=2)=[N:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-4-chloro-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate (330 mg, 0.89 mmol) in THF (10 mL) and H2O (3 mL) was added LiOH (100 mg, 4.16 mmol). The reaction mixture was stirred at 0° C. for 3 h and acidified with 1N HCl to pH=2-4. The resulting mixture was extracted with EtOAc (2×10 ml). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep HPLC to give the title compound as a white powder (15 mg, yield 5%). 1H NMR (400 MHz, DMSO-d6) δ 12.45 (s, 1H), 9.57 (s, 1H), 7.56 (m, 2H), 7.20 (s, 2H), 5.51 (m, 1H), 3.22 (m, 1H), 2.32 (s, 3H), 2.36 (m, 1H). MS (ESI) m/z=342 [M+H]+.

Workup

extractionThe resulting mixture was extracted with EtOAc (2×10 ml)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by prep HPLC

Sources & evidence

ORD record: ord-14fa1d77cd1045c8b500031a21e0aaca
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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