Acetonitrile → HCID 20712338, compound

HRID 2269324Notes

Reaction equation

HRID 2269324 reaction equation
C([O:4][NH:5][C:6]([CH:8]1[C:13]([OH:15])([CH3:14])[CH2:12][CH2:11][CH2:10][N:9]1[S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:7])C=C.C([O-])=O.C([NH+](CC)CC)C.C(#N)C>O>[OH:4][NH:5][C:6]([CH:8]1[C:13]([OH:15])([CH3:14])[CH2:12][CH2:11][CH2:10][N:9]1[S:16]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)=[CH:23][CH:24]=1)(=[O:18])=[O:17])=[O:7]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10219518Triethylazanium;formateHCID 54045369HCID 54045369, compound

Product 1

HCID 20712338HCID 20712338, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution 1-[4-(4-fluoro-benzyloxy)-benzenesulfonyl]-3-hydroxy-3-methyl-piperidine-2-carboxylic acid allyloxy-amide (0.14 g, 0.29 mmol), triethylammonium formate (0.35 mL of a 3M solution in water, 1.0 mmol) and acetonitrile (1.5 mL) was added tetrakistriphenylphosphine palladium (0.033 g, 0.029 mmol). After stirring for 30 min at 90-100° C., the mixture was cooled to room temperature and concentrated in vacuo and purified by silica gel chromatography eluting with 1:1 to 1:0 ethyl acetate-hexane, affording 0.030 g of 1-[4-(4-fluoro-benzyloxy)-benzenesulfonyl]-3-hydroxy-3-methyl-piperidine-2-carboxylic acid hydroxyamide as a colorless solid after trituration from CH2Cl2-hexane:

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel chromatography
  4. washeluting with 1:1 to 1:0 ethyl acetate-hexane

Sources & evidence

ORD record
ord-471cfef396b0491a9ad055f1f8d6ec36
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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