Hydrochloric Acid → 3-[4-(Azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide

HRID 20581노트

반응식

HRID 20581 반응식
Cl.[N:2]1([C:6]([C:8]2[CH:41]=[CH:40][C:11]([O:12][C:13]3[CH:14]=[C:15]([CH:25]=[C:26]([O:28][C@@H:29]([CH3:39])[CH2:30][O:31][Si](C(C)(C)C)(C)C)[CH:27]=3)[C:16]([NH:18][C:19]3[S:23][N:22]=[C:21]([CH3:24])[N:20]=3)=[O:17])=[C:10]([F:42])[CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3]1.C(=O)(O)[O-].[Na+]>CO>[N:2]1([C:6]([C:8]2[CH:41]=[CH:40][C:11]([O:12][C:13]3[CH:14]=[C:15]([CH:25]=[C:26]([O:28][C@@H:29]([CH3:39])[CH2:30][OH:31])[CH:27]=3)[C:16]([NH:18][C:19]3[S:23][N:22]=[C:21]([CH3:24])[N:20]=3)=[O:17])=[C:10]([F:42])[CH:9]=2)=[O:7])[CH2:3][CH2:4][CH2:5]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 593468823-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide

생성물 1

HCID 117200553-[4-(Azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide수율 52%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

10% Hydrochloric acid (2 mL) was added to a solution of 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide (950 mg, 1.58 mmol) in methanol (20 mL). The reaction was stirred at ambient temperature for 1 hour, saturated sodium bicarbonate solution added and the methanol evaporated. The aqueous residue was taken to pH2 and extracted with ethyl acetate. The extracts were combined, washed with brine, dried (MgSO4), filtered and evaporated in vacuo to give the crude product which was chromatographed on silica, eluting with ethyl acetate, to give the desired compound (400 mg) which was recrystallised from ethyl acetate (mpt 173° C.-175° C.).

후처리

  1. customthe methanol evaporated
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give the crude product which
  8. customwas chromatographed on silica
  9. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-a0fd83da55a34518ba3c211f4b2d24ab
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

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