(S)-2-tert-butoxycarbonylaminopropionimidic acid ethyl ester → [(S)-1-((S)-6-Fluoro-3-methyl-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethyl]carbamic acid tert-butyl ester

HRID 243232ノート

反応式

HRID 243232 の反応式
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([CH3:12])[NH:7][C:6]=2[C:5]([NH2:13])=[CH:4][CH:3]=1.C(O[C:17](=N)[C@@H:18]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH3:19])C>CCO>[C:24]([O:23][C:21](=[O:22])[NH:20][C@H:18]([C:17]1[N:7]2[C:6]3[C:11]([O:10][CH2:9][C@@H:8]2[CH3:12])=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[N:13]=1)[CH3:19])([CH3:27])([CH3:26])[CH3:25]

参加物

4

反応物 2

HCID 45092259(S)-2-tert-butoxycarbonylaminopropionimidic acid ethyl esterHCID 68158155(S)-8-Fluoro-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamine

生成物 1

HCID 68158968[(S)-1-((S)-6-Fluoro-3-methyl-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethyl]carbamic acid tert-butyl ester収率 76.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
75 °C

実験手順

(S)-8-Fluoro-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamine (160 mg, 0.86 mmol) was added to a solution of (S)-2-tert-butoxycarbonylaminopropionimidic acid ethyl ester (570 mg, 2.64 mmol) in EtOH (10 mL) and the reaction was heated at 75° C. for 60 min. The reaction mixture was concentrated in vacuo, and the residue was partitioned between DCM and sat. NaHCO3. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 0-40% DCM in cyclohexane) to afford the title compound as an off-white foam (220 mg, 76%). LCMS (Method J): RT=2.50 min, [M+H]+=336.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between DCM and sat. NaHCO3
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3328744f466141baafb0b12154c8ee98
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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