Hydrochloric Acid → HCID 58292669, compound

HRID 1798257Notes

Reaction equation

HRID 1798257 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:27][C:28]3[CH:33]=[N:32][CH:31]=[CH:30][N:29]=3)[CH:14]=[C:15]([O:16][CH2:17][CH2:18][NH:19]C(OC(C)(C)C)=O)[C:7]1=2)C.Cl>C(O)(=O)C>[NH2:19][CH2:18][CH2:17][O:16][C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:34])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([O:27][C:28]2[CH:33]=[N:32][CH:31]=[CH:30][N:29]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67253296HCID 67253296, compound

Product 1

HCID 58292669HCID 58292669, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [4-(2-tert-butoxycarbonylamino-ethoxy)-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (47 mg) in acetic acid (4 mL) was treated with 1N HCl (1 mL) at 100° C. 2 h. The reaction was concentrated to dryness. The residue was purified by preparative HPLC to give the title compound (22 mg) as a white solid. 1H NMR (300 MHz, CD3OD) δ 8.47 (s, 1H), 8.34-8.33 (m, 1H), 8.17-8.15 (m, 1H), 7.08 (d, J=1.8 Hz, 1H), 7.04 (d, J=1.8 Hz, 1H), 5.76-5.72 (m, 1H), 4.35-4.32 (m, 2H), 3.47-3.44 (m, 2H), 3.31-3.25 (m, 1H), 2.57-2.49 (m, 1H). MS calcd for (C15H16BN3O6+H)+: 346.2. MS found: (M+H)+=346.2.

Workup

  1. custom2 h
  2. concentrationThe reaction was concentrated to dryness
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d00bfca66ad04183ace989b4ae38b524
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…