Triphenylphosphine → [4-Aminomethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid

HRID 1798251Notes

Reaction equation

HRID 1798251 reaction equation
[N:1]([CH2:4][C:5]1[C:13]2[CH:12]([CH2:14][C:15]([OH:17])=[O:16])[O:11][B:10]([OH:18])[C:9]=2[CH:8]=[C:7]([O:19][C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)[CH:6]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][CH2:4][C:5]1[C:13]2[CH:12]([CH2:14][C:15]([OH:17])=[O:16])[O:11][B:10]([OH:18])[C:9]=2[CH:8]=[C:7]([O:19][C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 58292685[4-Azidomethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid

Product 1

HCID 50923242[4-Aminomethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acidYield 27.4%

Reagents, catalysts & solvents 1

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

Procedure

To a mixture of [4-azidomethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (100 mg, 0.29 mmol) was treated with PPh3 on resin (140 mg, about 0.42 mmol) in THF/water (5/1 mL). The reaction mixture was stirred at r.t overnight and filtered off. The filtrate was purified by HPLC, yielded 25 mg of the desired product. 1H NMR (300 MHz, CD3CN) δ 8.44 (s, 1H), 8.30 (d, 1H), 8.12 (s, 1H), 7.50 (s, 1H), 7.36 (s, 1H), 5.71 (m, 1H), 4.24 (s, 2H), 3.04-3.10 (m, 1H), 2.50-2.58 (m, 1H).

Workup

  1. filtrationfiltered off
  2. customThe filtrate was purified by HPLC

Sources & evidence

ORD record
ord-7c475d0daecb4d45a51bbd85dd9a9bf0
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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