Lithium Hydroxide → HCID 67252591, compound

HRID 1798197Notes

Reaction equation

HRID 1798197 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[OH-].[Li+]>C1COCC1.O>[C:31]([O:30][C:28]([NH:27][CH2:26][CH2:25][NH:24][C:20]1[N:19]=[C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:35])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)[CH:23]=[CH:22][N:21]=1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67253158HCID 67253158, compound

Product 1

HCID 67252591HCID 67252591, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of {6-[2-(2-tert-butoxycarbonylamino-ethylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid ethyl ester (0.35 g, 0.72 mmol) in THF (5 mL) was treated with lithium hydroxide (0.084 g, 3.60 mmol) in water (5 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour then at room temperature for 1 hour. The mixture was quenched with 2N HCl to pH 2 then concentrated to approximately half of the entire volume. The mixture was diluted with brine and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), filtered and concentrated to give {6-[2-(2-tert-butoxycarbonylamino-ethylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid, as a light yellow solid (0.18 g) after lyophilization. The aqueous layer was lyophilized, diluted with water (3 mL) and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), filtered and concentrated to a light yellow solid after lyophilization, to give a total of 0.21 g (64%) of product. 1H NMR (400 MHz, CD3OD) δ8.13 (d, J=6.64 Hz, 1H), 7.25 (s, 1H), 7.12 (s, 1H), 6.46 (m, 1H), 5.67 (dd, J=8.21, 2.40 Hz, 1H), 3.17 (dd, J=15.63, 3.13 Hz, 1H), 3.20-3.00 (m, 3H), 2.38 (br s, 4H), 1.40 (br s, 10H).

Workup

  1. waitat room temperature for 1 hour
  2. customThe mixture was quenched with 2N HCl to pH 2
  3. concentrationthen concentrated to approximately half of the entire volume
  4. additionThe mixture was diluted with brine
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-462252a169174077a9187902c86e7f15
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…