Ammonia → HCID 25132088, compound

HRID 339616Notes

Reaction equation

HRID 339616 reaction equation
[OH:1][B:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][C:15]([NH2:17])=[O:16])=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([CH2:18][N+:19]([O-])=O)[O:3]1.N.CC[OH:25]>[Ni]>[C:15]([OH:16])(=[O:25])[CH3:14].[NH2:19][CH2:18][CH:4]1[O:3][B:2]([OH:1])[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][C:15]([NH2:17])=[O:16])=[CH:8][CH:9]=[CH:10][C:5]1=2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 702Ethanol2×HCID 68646337HCID 68646337, compound

Product 1

HCID 25132088HCID 25132088, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of 4-(1-hydroxy-3-nitromethyl-1,3-dihydro-benzo[c][1,2]oxaborol-7-yloxy)-butyramide (50 mg, 0.17 mmol), Raney Ni (˜20 mg), 2 M NH3 in EtOH (1 mL), and EtOH (100 mL) was shaken under an atmosphere of H2 (42 psi) for 4.5 h at rt. The mixture was filtered through a bed of Celite and the filtrate was concentrated in vacuo. 3 N HCl in MeOH (1 mL) was added immediately to the residue and the resulting mixture was concentrated in vacuo. The residue was then purified by preparative HPLC (AcOH). The title compound was isolated as a white lyophilizate: yield 5 mg (111%).

Workup

  1. filtrationThe mixture was filtered through a bed of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. addition3 N HCl in MeOH (1 mL) was added immediately to the residue
  4. concentrationthe resulting mixture was concentrated in vacuo
  5. customThe residue was then purified by preparative HPLC (AcOH)

Sources & evidence

ORD record
ord-25374e2317644ac380c38702535a333f
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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