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

HRID 627197Notes

Reaction equation

HRID 627197 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]([OH:33])=O)[CH:20]=[C:19]1[CH2:34][C:35]([NH2:37])=[O:36])[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].[Cl-].[NH4+].C[N:41](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O.CCOC(C)=O>[CH2:1]([O:4][N:5]([CH:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C@H:21]([C:31](=[O:33])[NH2:41])[CH:20]=[C:19]1[CH2:34][C:35]([NH2:37])=[O:36])[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

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89851815(2S)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine-2-carboxylic acid

Product 1

HCID 89852287(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2S)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine-2-carboxylic acid (crude, 2.79 g, 5.16 mmol), ammonium chloride (552 mg, 10.32 mmol), HATU (3.93 g, 10.32 mmol) in DMF (20 mL) at 0° C., was added DIPEA (2.67 g, 20.65 mmol). After stirring at room temperature for 1 hr, 50 mL EtOAc and 50 mL water was added. The organic layer was washed with water, brine and dried over MgSO4, filtered and concentrated to give a residue, which was purified on silica gel column eluting with 0-100% ethyl acetate/hexanes to afford an off-white solid, 1.36 g, 49%.

Workup

  1. washThe organic layer was washed with water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue, which
  6. customwas purified on silica gel column
  7. washeluting with 0-100% ethyl acetate/hexanes
  8. customto afford an off-white solid, 1.36 g, 49%

Sources & evidence

ORD record
ord-ebe5fcb60a0a422f875c36ae8e94f2f0
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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