Hydrochloric Acid → HCID 58292698, compound

HRID 1798240Notes

Reaction equation

HRID 1798240 reaction equation
C(OC([NH:8][C:9]1[N:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[C:18]([CH3:30])[C:19]3[CH:23]([CH2:24][C:25]([OH:27])=[O:26])[O:22][B:21]([OH:28])[C:20]=3[CH:29]=2)=[N:13][CH:14]=1)=O)(C)(C)C.Cl.O1CCOCC1>>[NH2:8][C:9]1[N:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[C:18]([CH3:30])[C:19]3[CH:23]([CH2:24][C:25]([OH:27])=[O:26])[O:22][B:21]([OH:28])[C:20]=3[CH:29]=2)=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67252110HCID 67252110, compound

Product 1

HCID 58292698HCID 58292698, compoundYield 75%

Procedure

[6-(5-tert-Butoxycarbonylamino-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (70 mg, 0.17 mmol) was treated with 4M HCl in dioxane (1 mL, 4 mmol) and stirred at room temperature for 3 h. The reaction mixture was concentrated under vacuum and purified by HPLC affording the title compound (40 mg, 75%) as a white solid. 1H NMR (CD3OD) δ 7.79 (s, 1H), 7.64 (s, 1H), 7.02 (d, 1H), 6.98 (d, 1H), 5.65 (dd, 1H), 3.35 (m, 1H), 3.20 (dd, 1H), 2.36 (s, 3H). MS found: (M+H)+: 316.05.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-c76df76650554a3d8a4289e6754c96b5
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…