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

HRID 627198노트

반응식

HRID 627198 반응식
[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]

참가 물질

5

반응물 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)-carboxylate2회

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%.

후처리

  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%

출처 및 근거

ORD 기록
ord-c2df155884504cec9e5f3000576e0f63
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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