Trifluoroacetic acid → 2-(6-(Cyanomethoxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]-oxaborol-3-yl)acetic acid

HRID 1798119Notes

Reaction equation

HRID 1798119 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH3:23])[C:8]2[CH:12]([CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])[O:11][B:10]([OH:21])[C:9]=2[CH:22]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH3:23])[C:8]2[CH:12]([CH2:13][C:14]([OH:16])=[O:15])[O:11][B:10]([OH:21])[C:9]=2[CH:22]=1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67254401tert-Butyl 2-(6-(cyanomethoxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 509230902-(6-(Cyanomethoxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]-oxaborol-3-yl)acetic acidYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(6-(cyanomethoxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (120 mg, 0.38 mmol) in 5 ml DCM was added TFA (5 mL) at 0° C. The reaction mixture was stirred for 30 min at room temperature and concentrated to dryness. The residue was purified by prep HPLC to give the title compound as a white solid (60 mg, yield: 60.8%). 1H NMR (400 MHz, DMSO-d) δ12.31 (s, 1H), 9.24 (s, 1H), 7.16 (d, J=2.4 Hz, 1H), 6.97 (d, J=2.4 Hz, 1H), 5.48-5.45 (m, 1H), 5.15 (s, 2H), 3.06-3.02 (m, 1H), 2.28 (s, 3H), 2.12-2.05 (m, 1H); MS (ESI) m/z=262 [M+H]+.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-6738fc58ee634701b172ef8bdc664c5a
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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