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

HRID 627198Notes

Reaction equation

HRID 627198 reaction equation
[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]

Participants

5

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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%.

Workup

  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%

Sources & evidence

ORD record
ord-c2df155884504cec9e5f3000576e0f63
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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