Hydrochloric Acid → HCID 58292630, compound

HRID 1798207Notes

Reaction equation

HRID 1798207 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]([O: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.[Li+].[OH-].Cl>C1COCC1.O.O>[C:32]([O:31][C:29]([NH:28][CH2:27][CH2:26][CH2:25][O: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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292678HCID 58292678, compound

Product 1

HCID 58292630HCID 58292630, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of {6-[2-(3-tert-butoxycarbonylamino-propoxy)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid ethyl ester (0.45 g, 0.89 mmol) in THF:H2O (1:1, 6 mL) at 0° C. was added a solution of LiOH (0.043 g, 1.79 mmol) in water (1 mL). The solution was allowed to warm to room temperature over 3 hours then acidified to pH 4 with 1N HCl and extracted with EtOAc (2×10 mL). The organic extracts were dried and concentrated in vacuo to give crude {6-[2-(3-tert-Butoxycarbonylamino-propoxy)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.3 g) which was used without further purification. MS (ESI) m/z=472 [M−H]−.

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. customThe organic extracts were dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-955ef776e7414b0187864638eebf4349
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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