Hydrochloric Acid → HCID 58292627, compound

HRID 1798316Notes

Reaction equation

HRID 1798316 reaction equation
[S:1]1[CH:5]=[N:4][N:3]=[C:2]1[O:6][C:7]1[CH:8]=[C:9]([CH3:23])[C:10]2[C@@H:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13][B:12]([OH:21])[C:11]=2[CH:22]=1.C1COCC1.[Li+].[OH-].Cl>O.CO>[S:1]1[CH:5]=[N:4][N:3]=[C:2]1[O:6][C:7]1[CH:8]=[C:9]([CH3:23])[C:10]2[C@H:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13][B:12]([OH:21])[C:11]=2[CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58292738HCID 58292738, compound

Product 1

HCID 58292627HCID 58292627, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of (R)-ethyl 2-(6-(1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.9 g, 2.69 mmol) in a mixed solution of THF (30 mL) and methanol (4 mL) was added a solution of LiOH. H2O (0.57 g, 13.5 mmol) in water (30 mL) at 0° C. The resulting mixture was stirred at room temperature for 1.5 hrs and then acidified to pH=2 with diluted hydrochloric acid at 0° C. After removal of the volatile organics, the residue was dissolved in EtOAc. The aqueous phase was dried and concentrated in vacuo to give the products.

Workup

  1. customat 0° C
  2. customAfter removal of the volatile organics, the residue
  3. dissolutionwas dissolved in EtOAc
  4. customThe aqueous phase was dried
  5. concentrationconcentrated in vacuo
  6. customto give the products

Sources & evidence

ORD record
ord-b1473d92aa714c198dab963e9d7ea38a
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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