1,4-Dioxane hydrochloride → HCID 58292781, compound

HRID 1798164Notes

Reaction equation

HRID 1798164 reaction equation
C(OC([NH:8][C:9]1[CH: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[CH: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

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67253650HCID 67253650, compound

Product 1

HCID 58292781HCID 58292781, compoundYield 81.2%

Procedure

[6-(5-tert-Butoxycarbonylamino-pyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (26 mg) was treated with HCl/dioxane (0.5 mL) at room temperature for 2 h. The reaction was concentrated to dryness. The residue was purified by preparative HPLC to give the title compound (16 mg). 1H NMR (300 MHz, CD3OD) δ 7.66 (s, 1H), 7.23 (d, J=7.8 Hz, 1H), 7.00 (s, 1H), 6.96 (s, 1H), 6.78 (d, J=7.8 Hz, 1H), 5.68-5.64 (m, 1H), 3.20-3.14 (m, 1H), 2.36 (s, 3H), 2.34-2.26 (m, 1H). MS calcd for (C15H15BN2O5+H)+: 315.1. MS found: (M+H)+=315.1.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7f3ffc34e69b4586b03b636b72a1c442
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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