HCID 58292703, compound → HCID 58292733, compound

HRID 1798158Notes

Reaction equation

HRID 1798158 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:32]=[CH:33][CH:34]=1)[O:16][C:17]1[CH:18]=[C:19]([CH3:31])[C:20]2[CH:24]([CH2:25][C:26]([OH:28])=[O:27])[O:23][B:22]([OH:29])[C:21]=2[CH:30]=1)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:32]=[CH:33][CH:34]=1)[O:16][C:17]1[CH:18]=[C:19]([CH3:31])[C:20]2[CH:24]([CH2:25][C:26]([OH:28])=[O:27])[O:23][B:22]([OH:29])[C:21]=2[CH:30]=1

Participants

4

Reactant 1

HCID 58292703HCID 58292703, compound

Product 1

HCID 58292733HCID 58292733, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of {6-[3-(3-tert-butoxycarbonylamino-propoxy)-phenoxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.5 g, 1.06 mmol) in 4M HCl in dioxane (5 mL) was stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo and the residue purified by preparative HPLC to give {6-[3-(3-amino-propoxy)-phenoxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.18 g, 45%). 1H NMR (400 MHz, DMSO): δ 8.36 (s, 1H), 7.24 (t, J=8.4 Hz, 1H), 6.99 (s, 1H), 6.85 (s, 1H), 6.66 (d, J=8.0 Hz, 1H), 6.51 (t, J=8.0 Hz, 2.0H), 5.37 (d, J=6.0 Hz, 1H), 3.98 (t, J=5.6 Hz, 2H), 2.85 (d, J=12.0 Hz, 2H), 2.22 (s, 3H), 2.05-1.93 (m, 4H). MS (ESI) m/z=372 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-412d2f11289749e3a62b57993b0d1647
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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