Hydrochloric Acid → HCID 58292645, compound

HRID 1798258Notes

Reaction equation

HRID 1798258 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:28][C:29]3[CH:34]=[N:33][CH:32]=[CH:31][N:30]=3)[CH:14]=[C:15]([O:16][CH2:17][CH2:18][CH2:19][NH:20]C(OC(C)(C)C)=O)[C:7]1=2)C.Cl>C(O)(=O)C>[NH2:20][CH2:19][CH2:18][CH2:17][O:16][C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:35])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([O:28][C:29]2[CH:34]=[N:33][CH:32]=[CH:31][N:30]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58292875HCID 58292875, compound

Product 1

HCID 58292645HCID 58292645, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [4-(3-tert-butoxycarbonylamino-propoxy)-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (81 mg) in acetic acid (4 mL) was treated with 1N HCl (1 mL) at 100° C. for 2 h. The reaction was concentrated to dryness. The residue was purified by preparative HPLC to give the title compound (32 mg) as a white solid. 1H NMR (300 MHz, CD3OD) δ 8.42 (s, 1H), 8.31-8.30 (m, 1H), 8.17-8.15 (m, 1H), 6.98 (d, J=1.5 Hz, 1H), 6.90 (d, J=1.5 Hz, 1H), 5.66-5.62 (m, 1H), 4.16 (t, 2H), 3.19 (t, 2H), 3.17-3.09 (m, 1H), 2.47-2.39 (m, 1H), 2.23-2.21 (m, 2H). MS calcd for (C16H18BN3O6+H)+:360.2. MS found: (M+H)+=360.2.

Workup

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

Sources & evidence

ORD record
ord-558f97be2403454bae95f95f6455f715
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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