Lithium Hydroxide → HCID 50923088, compound

HRID 1798115Notes

Reaction equation

HRID 1798115 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][CH2:13][C:14]([NH:16][CH3:17])=[O:15])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:18][C:19]([O:21]CC)=[O:20])[O:3]1.[Li+].[OH-]>C1COCC1.CO.O>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][CH2:13][C:14]([NH:16][CH3:17])=[O:15])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:18][C:19]([OH:21])=[O:20])[O:3]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58292707HCID 58292707, compound

Product 1

HCID 50923088HCID 50923088, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The mixture of ethyl 2-(1-hydroxy-4-methyl-6-(2-(methylamino)-2-oxoethoxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (321 mg, 1 mmol), LiOH (119.5 mg, 5 mmol) in THF/MeOH/H2O (5 ml/5 ml/10 ml) was stirred at room temperature for 4 hrs. The reaction mixture was quenched with 3N HCl. Filter the precipitate and washed with water. Dried to give desired product 150 mg as white powder. 1H NMR (400 MHz, DMSO-d6) δ 12.3 (s, 1H), 9.14 (s, 1H), 7.97 (s, 1H), 7.01 (s, 1H), 6.88 (s, 1H), 5.42 (d, J=9.6 Hz, 1H), 4.42 (s, 2H), 3.20 (dd, J=15.6, 2.4 Hz, 1H), 2.63 (d, J=3 Hz, 3H), 2.48 (s, 3H), 2.05 (dd, J=9.6, 15.6 Hz, 1H). MS (ESI) m/z=292 [M−H]−.

Workup

  1. customThe reaction mixture was quenched with 3N HCl
  2. filtrationFilter the precipitate
  3. washwashed with water
  4. customDried

Sources & evidence

ORD record
ord-a65630deb3be49d0abad8580e079f7aa
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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