Hydrochloric Acid → [4-Azidomethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid

HRID 1798255Notes

Reaction equation

C([O:3][C:4](=[O:27])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:20][C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)[CH:14]=[C:15]([CH2:16][N:17]=[N+:18]=[N-:19])[C:7]1=2)C.Cl>CC(O)=O>[N:17]([CH2:16][C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:27])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([O:20][C:21]2[CH:26]=[N:25][CH:24]=[CH:23][N:22]=2)[CH:14]=1)=[N+:18]=[N-:19]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of [4-azidomethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (200 mg, 0.54 mmol) was added 1N HCl (5 mL) and AcOH (20 mL). The mixture was heated at 100° C. for 4 h. The acid was removed under vacuum and the crude product was purified by HPLC, yielded 100 mg of desire product. 1H NMR (300 MHz, CD3CN) δ 8.59 (s, 1H), 8.44 (s, 1H), 8.23 (s, 1H), 8.20 (s, 1H), 7.59 (s, 1H), 7.43 (s, 1H), 5.81 (dd, 1H), 4.54-4.72 (m, 2H), 3.23-3.29 (m, 2H), 2.49-2.58 (dd, 2H), 2.08 (t, 3H).

Workup

customThe acid was removed under vacuum
customthe crude product was purified by HPLC
customyielded 100 mg of desire product

Sources & evidence

ORD record: ord-3068157c3a9948b4a5c2f94741592cfe
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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