Hydrochloric Acid → (4-Aminomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid

HRID 1798087Notes

Reaction equation

HRID 1798087 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:20])[CH:14]=[C:15]([CH2:16][N:17]=[N+]=[N-])[C:7]1=2)C.Cl>C1COCC1.O.[Pd]>[NH2:17][CH2:16][C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:21])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([OH:20])[CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58292573(4-Azidomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Product 1

HCID 58292686(4-Aminomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acidYield 16.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of (4-azidomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (15 mg) in THF/water (2:1, 1 mL) was added 10% Pd/C (5 mg), and a drop of 1N HCl. The reaction was degassed and stirred under hydrogen overnight and filtered off. The filtrate was purified by HPLC, yielded 2 mg of product. MS (ESI) m/z: 237.9 [M+1]+; 1H NMR (300 MHz, CD3OD) δ 8.25 (s, 3H), 7.06 (d, 1H), 6.98 (d, 1H), 8.20 (s, 1H), 5.68 (dd, 1H), 4.17 (s, 2H), 3.67 (s, 1H), 2.99-3.04 (m, 1H), 2.71-2.87 (m, 2H), 2.45-2.52 (m, 1H).

Workup

  1. customThe reaction was degassed
  2. filtrationfiltered off
  3. customThe filtrate was purified by HPLC

Sources & evidence

ORD record
ord-f4d43a12f01d49989559947932b651e4
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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