Boron tribromide → (7-Hydroxy-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid

HRID 30986Notes

Reaction equation

HRID 30986 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][C:6]1[NH:11][C:10]2[CH:12]=[CH:13][C:14]([O:16]C)=[CH:15][C:9]=2[S:8](=[O:19])(=[O:18])[N:7]=1)C.B(Br)(Br)Br>ClCCl>[OH:16][C:14]1[CH:13]=[CH:12][C:10]2[NH:11][C:6]([CH2:5][C:4]([OH:20])=[O:3])=[N:7][S:8](=[O:19])(=[O:18])[C:9]=2[CH:15]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 46941516Ethyl (7-methoxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)acetate

Product 1

HCID 11368865(7-Hydroxy-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetic acidYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 4a (1 g, 3.7 mmol) in dichloromethane (23 mL), a solution of 1.0 M of BBr3 in dichloromethane was added dropwise at 0° C. over 5 minutes. The reaction mixture was stirred at 0° C. to room temperature overnight. LC-MS result confirmed the completion of the reaction. The reaction mixture was poured onto 50 mL of ice which was extracted with EtOAc (150 mL×3). The combined organic layer was dried over MgSO4, filtered, concentrated under reduced pressure and further dried under high vacuum to give 826.8 mg of desired product (10c) as brown foam in 87.2% yield. This crude product was directly used in next step without further purification. LC-MS: (ESI+) m/e=257.10 [M+1]+ (exact ms: 256.02).

Workup

  1. customLC-MS result
  2. customthe completion of the reaction
  3. extractionwas extracted with EtOAc (150 mL×3)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-e05b82e2939144c3bf80a1b667ac483b
Source dataset
uspto-grants-2008_09
Patent number
US07425552B2

Reaction notes

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