Hydrochloric Acid → [6-(5-Amino-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid

HRID 1798294Notes

Reaction equation

HRID 1798294 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[S:19][C:20]([NH2:23])=[N:21][N:22]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.CO.O>[NH2:23][C:20]1[S:19][C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:24])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:22][N:21]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292641Ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292594[6-(5-Amino-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acidYield 75%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution [6-(5-amino-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.6 g, 1.72 mmol) in THF (15 mL) and methanol (2 mL) was added a solution of LiOH (0.165 g, 6.87 mmol) in water (15 mL) at 0° C. The resulting mixture was stirred at room temperature for 1.5 hours then acidified to pH=2 with dilute hydrochloric acid at 0° C. After removal of the volatile organics, the residue was neutralized to pH 7 using saturated sodium bicarbonate. The precipitated solid was filtered and stirred with ethyl acetate (20 mL) for 1 hour. The solid was filtered, washed with cold ethyl acetate and water then dried to give the product (0.412 g, 75%). 1HNMR (400 MHz, DMSO-d6) δ9.26 (br. s., 1H), 7.32 (d, J=2.05 Hz, 1H), 7.16 (d, J=1.76 Hz, 1H), 7.05 (s, 2H), 5.48 (dd, J=9.37, 2.05 Hz, 1H), 3.04 (dd, J=15.37, 2.49 Hz, 1H), 2.29 (s, 3H), 2.12 (dd, 1H). MS (ESI) m/z=322 [M+H]+.

Workup

  1. customAfter removal of the volatile organics, the residue
  2. filtrationThe precipitated solid was filtered
  3. stirringstirred with ethyl acetate (20 mL) for 1 hour
  4. filtrationThe solid was filtered
  5. washwashed with cold ethyl acetate and water
  6. customthen dried

Sources & evidence

ORD record
ord-794ecd84a0ff4cd49c34ed59c4e6191a
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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