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

HRID 30986노트

반응식

HRID 30986 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e05b82e2939144c3bf80a1b667ac483b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425552B2

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