Pyridine → HCID 57005544, compound

HRID 2269353Notes

Reaction equation

HRID 2269353 reaction equation
[CH:1]([N:3]([O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)[C@@H:4]([CH3:22])[C@@H:5]([CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[C:6]([OH:8])=[O:7])=[O:2].N1C=CC=CC=1.FC(F)(F)C(O[C:41]1[C:46]([F:47])=[C:45]([F:48])[C:44]([F:49])=[C:43]([F:50])[C:42]=1[F:51])=O>ClCCl>[CH:1]([N:3]([O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)[C@@H:4]([CH3:22])[C@@H:5]([CH2:9][CH:10]1[CH2:11][CH2:12][CH:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:14][CH2:15]1)[C:6]([O:8][C:41]1[C:42]([F:51])=[C:43]([F:50])[C:44]([F:49])=[C:45]([F:48])[C:46]=1[F:47])=[O:7])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 20712412HCID 20712412, compound

Product 1

HCID 57005544HCID 57005544, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(4-phenylcyclohexylmethyl)butanoic acid (3.65 g, 0.009 mol) in dichloromethane (20 mL) at 25° C. is added via syringe pyridine (0.87 g, 0.011 mol) followed by pentafluorophenyl trifluoroacetate (3.1 g, 0.011 mol). The mixture is stirred for 6 h, diluted with dichloromethane and washed with 0.1 M aqueous HCl, 1 M aqueous sodium carbonate, saturated aqueous sodium chloride and dried over sodium sulfate. Concentration in vacuo followed by chromatography on silica gel with hexanes-EtOAc (2:1) as eluent gives 3.05 g (60%) of pentafluorophenyl (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(4-phenylcyclohexylmethyl)butanoate as an oil.

Workup

  1. washwashed with 0.1 M aqueous HCl, 1 M aqueous sodium carbonate, saturated aqueous sodium chloride
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-47688ba1e6ca4ec5bde7d49a5b985766
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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