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 20581ノート

反応式

HRID 20581 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-a0fd83da55a34518ba3c211f4b2d24ab
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

反応ノート

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