Sodium Chloride → HCID 86656359, compound

HRID 1942495Notes

Reaction equation

HRID 1942495 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:19]([OH:21])=O)[C:16]([CH3:18])=[CH:17][C:12]=2[S:11][CH:10]([CH3:22])[C:9]1=[O:23])=[O:4].C(N(C(C)C)C(C)C)C.[CH:33]([NH:36][C@@H:37]1[CH2:42][CH2:41][CH2:40][N:39]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:38]1)([CH3:35])[CH3:34].[Cl-].[Na+]>CN(C)C=O>[CH:33]([N:36]([C:19]([C:15]1[C:16]([CH3:18])=[CH:17][C:12]2[S:11][CH:10]([CH3:22])[C:9](=[O:23])[N:8]([CH2:7][CH2:6][NH:5][C:3]([O:2][CH3:1])=[O:4])[C:13]=2[CH:14]=1)=[O:21])[C@@H:37]1[CH2:42][CH2:41][CH2:40][N:39]([C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44])[CH2:38]1)([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 53256475HCID 53256475, compoundHCID 67332596HCID 67332596, compound

Product 1

HCID 86656359HCID 86656359, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-{2-[(methoxycarbonyl)amino]ethyl}-2,7-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid (460 mg) in N,N-dimethylformamide (4 ml) were added CIP reagent, N-ethyldiisopropylamine, tert-butyl (3R)-3-(isopropylamino)piperidine-1-carboxylate, and the mixture was stirred overnight. After the reaction was complete, to the mixture was added a saturated aqueous sodium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (284 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d1a58014e0a4ccd92a6db2b32ef658d
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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