Lithium Hydroxide → HCID 50923089, compound

HRID 1798103Notes

Reaction equation

HRID 1798103 reaction equation
[NH2:1][CH2:2][C:3]1[C:11]2[CH:10]([CH2:12][C:13]([O:15]CC)=[O:14])[O:9][B:8]([OH:18])[C:7]=2[CH:6]=[C:5]([O:19][CH3:20])[CH:4]=1.[Li+].[OH-]>C1COCC1.CO.O>[NH2:1][CH2:2][C:3]1[C:11]2[CH:10]([CH2:12][C:13]([OH:15])=[O:14])[O:9][B:8]([OH:18])[C:7]=2[CH:6]=[C:5]([O:19][CH3:20])[CH:4]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58292695HCID 58292695, compound

Product 1

HCID 50923089HCID 50923089, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The mixture of ethyl 2-(4-(aminomethyl)-1-hydroxy-6-methoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (20 mg), LiOH (24 mg, 1 mmol) in THF/MeOH/H2O (1.5 ml/1.5 ml/1.5 ml) was stirred at room temperature for 2 hrs. The solvent was removed in reduced pressure to dryness. The crude product was purified by Prep-HPLC to give desired product 5 mg as white powder (TFA salt). 1H NMR (400 MHz, DMSO-d6) δ 9.27 (s, 1H), 8.22 (brs, 3H), 7.19 (d, J=2.4 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H), 5.60 (dd, J=9.4, 2.2 Hz, 1H), 4.04 (q, J=4.5 Hz, 2H), 3.78 (s, 3H), 2.99 (dd, J=15.8, 2.4 Hz, 1H), and 2.11 (dd, J=9.4, 15.8 Hz, 1H). MS (ESI) m/z=252 [M+H]+.

Workup

  1. customThe solvent was removed in reduced pressure to dryness
  2. customThe crude product was purified by Prep-HPLC

Sources & evidence

ORD record
ord-6a156f3037c841778ace9dc61b9d2c9c
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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