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

HRID 30986ノート

反応式

HRID 30986 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e05b82e2939144c3bf80a1b667ac483b
出典データセット
uspto-grants-2008_09
特許番号
US07425552B2

反応ノート

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