Lithium Hydroxide → HCID 67253348, compound

HRID 1798199Notes

Reaction equation

HRID 1798199 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][CH2:26][CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[OH-].[Li+]>C1COCC1.O>[C:32]([O:31][C:29]([NH:28][CH2:27][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:36])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)[CH:23]=[CH:22][N:21]=1)=[O:30])([CH3:34])([CH3:35])[CH3:33]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67253132HCID 67253132, compound

Product 1

HCID 67253348HCID 67253348, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of {6-[2-(3-tert-butoxycarbonylamino-propylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid ethyl ester (0.39 g, 0.78 mmol) in THF (10 mL) was treated with lithium hydroxide (0.089 g, 3.90 mmol) in water (2 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 in vacuo. The residue was diluted with brine and extracted with ethyl acetate. The organic extracts were dried (Na2SO4), filtered and concentrated to give {6-[2-(3-tert-butoxycarbonylamino-propylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid as a yellow solid (0.27 g, 74%) after lyophilization. 1H NMR (400 MHz, CD3OD) δ8.09 (d, J=6.25 Hz, 1H), 7.22 (s, 1H), 7.10 (s, 1H), 6.32 (m, 1H), 5.67 (d, J=6.25 Hz, 1H), 3.28-3.14 (br m, 2H), 3.17 (dd, J=15.24, 2.35 Hz, 1H), 3.10-2.90 (m, 2H), 2.38 (s, 3H), 2.36-2.25 (m, 1H), 1.70-1.50 (m, 2H), 1.41 (s, 9H).

Workup

  1. waitat room temperature for 1 hour
  2. customThe mixture was quenched with 2N HCl to pH 2
  3. concentrationthen concentrated in vacuo
  4. additionThe residue 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-233ac9d2869346d2aa211370fce2a663
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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