Hydrochloric Acid → (R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-1,4-oxazepan-3-one

HRID 403253ノート

反応式

HRID 403253 の反応式
C(=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:32])=[C:19]([C@:21]2([CH3:31])[C:27]([F:29])([F:28])[CH2:26][O:25][CH2:24][C:23](=[O:30])[NH:22]2)[CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:32])=[C:19]([C@:21]2([CH3:31])[C:27]([F:28])([F:29])[CH2:26][O:25][CH2:24][C:23](=[O:30])[NH:22]2)[CH:20]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86670909(R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-6,6-difluoro-5-methyl-[1,4]oxazepan-3-one

生成物 1

HCID 68226741(R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-1,4-oxazepan-3-one収率 90%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of (R)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-6,6-difluoro-5-methyl-[1,4]oxazepan-3-one (intermediate A17D) (308 mg, 0.70 mmol) in dioxane (20 ml) at 23° C. was added 1 M HCl (2.1 ml, 2.1 mmol) was added. After 30 min of stirring, the reaction mixture was poured on sat. NaHCO3-solution and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to give a dark green oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the (R)-5-(5-amino-2-fluorophenyl)-6,6-difluoro-5-methyl-1,4-oxazepan-3-one (172 mg, 0.63 mmol, 90%) as a yellow foam. MS (ISP): m/z=275.2 [(M+H)+].

後処理

  1. additionwas added
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a dark green oil, which
  8. customwas purified by silica gel column chromatography with n-heptane/ethyl acetate

出典と根拠

ORDレコード
ord-11a21038385a4f328396c2e7654a45b9
出典データセット
uspto-grants-2014_06
特許番号
US08748418B2

反応ノート

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