Triethylamine → HCID 53855238, compound

HRID 1359031Notes

Reaction equation

HRID 1359031 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C@@H:7]([C:22](O)=[O:23])[CH2:6]1)=[O:4].Cl.[CH2:26]([O:33][NH2:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)(=[O:12])=[O:13])[C@@H:7]([C:22](=[O:23])[NH:34][O:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 70024088HCID 70024088, compound

Product 1

HCID 53855238HCID 53855238, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2R,4R)-1-(4-methoxy-benzenesulfonyl)-piperidine-2,4-dicarboxylic acid 4-methyl ester (4.4 g, 12.3 mmol), O-benzylhydroxylamine hydrochloride (2.15 g, 13.5 mmol), and triethylamine (5.15 mL, 36.9 mmol) was added benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (6.0 g, 12.3 mmol) at ambient temperature. The resulting mixture was stirred for 24 hours. The mixture was diluted with ethyl acetate and washed with 1 M aqueous hydrogen chloride, aqueous sodium bicarbonate, and brine. The organic mixture was dried over magnesium sulfate, filtered, and the filtrate was concentrated. The crude residue was purified by silica gel chromatography (elution with 5% methanol in methylene chloride) to provide (2R,4R)-2-benzyloxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-piperidine-4-carboxylic acid methyl ester as a colorless solid.

Workup

  1. washwashed with 1 M aqueous hydrogen chloride, aqueous sodium bicarbonate, and brine
  2. dry with materialThe organic mixture was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe crude residue was purified by silica gel chromatography (elution with 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-c9b836d0891d419a9487d1c9887e4985
Source dataset
uspto-grants-2003_07
Patent number
US06599890B1

Reaction notes

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