Thiophenol → (2S)-tert-butyl 5-((allyloxy)amino)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627198ノート

反応式

HRID 627198 の反応式
[CH2:1]([O:4][N:5]([CH:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31](=[O:33])[NH2:32])[CH:20]=[C:19]1[CH2:34][C:35]([NH2:37])=[O:36])S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>C(#N)C>[CH2:1]([O:4][NH:5][CH:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31](=[O:33])[NH2:32])[CH:20]=[C:19]1[CH2:34][C:35]([NH2:37])=[O:36])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 89852287(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate2 回

生成物 1

HCID 89851408(2S)-tert-butyl 5-((allyloxy)amino)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of (2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 175, 1.36 g, 2.52 mmol) and potassium carbonate (1.742 g, 12.60 mmol) in acetonitrile (20.0 mL) at 0° C. was added benzenethiol (1.389 g, 12.60 mmol). The mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated and the resulting residue was triturated with DCM. The solids were removed by filtration. The filtrate was concentrated to a pale yellow film, which was subjected to silica gel column eluting with 0-50% MeOH/DCM to give a pale yellow solid, 330 mg, 36.9%.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was triturated with DCM
  3. customThe solids were removed by filtration
  4. concentrationThe filtrate was concentrated to a pale yellow film, which
  5. washeluting with 0-50% MeOH/DCM
  6. customto give a pale yellow solid, 330 mg, 36.9%

出典と根拠

ORDレコード
ord-c2df155884504cec9e5f3000576e0f63
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

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