Hydrochloric Acid → HCID 58292703, compound

HRID 1798157Notes

Reaction equation

HRID 1798157 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][CH: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])[CH: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[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[O:17][C:13]1[CH:14]=[C:15]([CH3:16])[C:7]2[CH:6]([CH2:5][C:4]([OH:36])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=1)=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292857HCID 58292857, compound

Product 1

HCID 58292703HCID 58292703, compound

Reagents, catalysts & solvents 2

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

Procedure

To a solution of {6-[3-(3-tert-butoxycarbonylamino-propoxy)-phenoxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid ethyl ester (0.6 g, 1.2 mmol) in THF:H2O (1:1, 10 mL) at 0° C. was added a solution of LiOH (0.086 g, 3.6 mmol) in water (1 mL). The solution was allowed to warm to room temperature over 3 hours then acidified to pH 2 with 1N HCl at 0° C. and extracted with EtOAc (2×10 mL). The organic extracts were dried and concentrated in vacuo to give crude 6-[3-(3-tert-butoxycarbonylamino-propoxy)-phenoxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.5 g) which was used without further purification MS (ESI) m/z=470 [M−H]−.

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. customThe organic extracts were dried
  3. concentrationconcentrated in vacuo
  4. customto give crude 6-[3-(3-tert-butoxycarbonylamino-propoxy)-phenoxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid (0.5 g) which
  5. customwas used without further purification MS (ESI) m/z=470 [M−H]−

Sources & evidence

ORD record
ord-4a66d83d5c8d42d09d26e09d07fb1728
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…