Lithium Hydroxide → HCID 67254018, compound

HRID 1798202Notes

Reaction equation

HRID 1798202 reaction equation
C([O:3][C:4](=[O:36])[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][C:26]4[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=4[O:34][CH3:35])[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[OH-].[Li+]>C1COCC1.O>[CH3:35][O:34][C:27]1[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:26]=1[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:36])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)[CH:23]=[CH:22][N:21]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67253094HCID 67253094, compound

Product 1

HCID 67254018HCID 67254018, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of {6-[2-(2,5-dimethoxy-benzylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid ethyl ester (0.35 g, 0.71 mmol) in THF (5 mL) was treated with lithium hydroxide (0.081 g, 3.55 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 ½ the entire volume, diluted with brine and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), filtered and concentrated to give {6-[2-(2,5-dimethoxy-benzylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid as a yellow solid (0.32 g, 97%). 1H NMR (400 MHz, CD3OD) δ8.11 (d, J=6.64 Hz, 1H), 7.25 (s, 1H), 7.13 (s, 1H), 6.60-6.20 (m, 4H), 5.75-5.65 (m, 1H), 4.20-4.10 (m, 2H), 3.80 (s, 3H), 3.76 (s, 3H), 3.21-3.10 (m, 1H), 2.40 (s, 3H), 2.39-2.20 (m, 1H).

Workup

  1. waitat room temperature for 1 hour
  2. customThe mixture was quenched with 2N HCl to pH 2
  3. concentrationthen concentrated
  4. additiondiluted 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-e93db3c09c10495793870906d7b3ed50
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…