Hydrochloric Acid → 4-Chloro-3-fluoro-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzenesulfonamide

HRID 1987581노트

반응식

HRID 1987581 반응식
C([O:3][C:4](=O)[CH:5]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([F:26])[CH:20]=1)(=[O:18])=[O:17])[CH:6]([C:11]([F:14])([F:13])[F:12])[C:7]([F:10])([F:9])[F:8])C.[Li+].[BH4-].Cl>C1COCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([S:16]([NH:15][CH:5]([CH2:4][OH:3])[CH:6]([C:7]([F:8])([F:9])[F:10])[C:11]([F:14])([F:12])[F:13])(=[O:17])=[O:18])=[CH:20][C:21]=1[F:26]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydride2회HCID 866160062-(4-Chloro-3-fluoro-benzenesulfonylamino)-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester

생성물 1

HCID 247657434-Chloro-3-fluoro-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzenesulfonamide수율 81.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

2-(4-Chloro-3-fluoro-benzenesulfonylamino)-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester (150 mg, 0.337 mmol) was dissolved in anhydrous THF (5 mL) and cooled to 0° C. 2M LiBH4 in THF (168 μL in THF) was added and the solution allowed to warm to 25° C. After 18 h, LC-MS revealed unreacted starting ester present. Additional 2M LiBH4 (200 μL) was added and the solution stirred for 24 h. The solution was cooled in an ice bath and 1N hydrochloric acid was added to quench the reaction. The solvent was removed in vacuo and the aqueous phase transferred to a separatory funnel with EtOAc (100 mL) and washed with distilled water (100 mL). The organic layer was removed and the aqueous phase extracted with EtOAc (100 mL×2). The organic extracts were combined, dried (MgSO4), filtered and evaporated to give a white solid (111 mg). This material was purified by Gilson RP-HPLC (column YMC Combiprep 50×20 mm, gradient 10-100% CH3CN: H2O) to afford a white solid (63 mg, 46%). Mass Spectrum (+ESI): 401.8 [M−H]+.

후처리

  1. temperatureto warm to 25° C
  2. temperatureThe solution was cooled in an ice bath
  3. customto quench
  4. customthe reaction
  5. customThe solvent was removed in vacuo
  6. customthe aqueous phase transferred to a separatory funnel with EtOAc (100 mL)
  7. washwashed with distilled water (100 mL)
  8. customThe organic layer was removed
  9. extractionthe aqueous phase extracted with EtOAc (100 mL×2)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customevaporated

출처 및 근거

ORD 기록
ord-2d67a7dbfc764d90b3b7f9882db3b368
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550629B2

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