(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-3-ethyl-5,6-dihydropyridine-1(2H)-carboxylate → (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-ethyl-1,2,5,6-tetrahydropyridine-2-carboxamide

HRID 627225Notes

Reaction equation

HRID 627225 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([C:31](=[O:33])[NH2:32])[C:20]([CH2:34][CH3:35])=[CH:19]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].C(ON([C@H]1CN[C@H](C(N)=O)C=C1C)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)C=C>ClCCl>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][NH:22][C@H:21]([C:31]([NH2:32])=[O:33])[C:20]([CH2:34][CH3:35])=[CH:19]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 89852230(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-3-ethyl-5,6-dihydropyridine-1(2H)-carboxylate2×HCID 117940244(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide

Product 1

HCID 89852009(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-ethyl-1,2,5,6-tetrahydropyridine-2-carboxamideYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-3-ethyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 212, 1.44 g, 2.82 mmol) following the procedure described for Intermediate 21, except the reaction mixture was stirred over the weekend at room temperature. The reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate. An emulsion formed and the aqueous was extracted three to four more times with DCM. The organics were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford the title compound (0.870 g, 75%) as a yellow foam.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. customAn emulsion formed
  3. extractionthe aqueous was extracted three to four more times with DCM
  4. washThe organics were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5827e09ed81e42f2bad0f2570b5e659f
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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