Pyridine → HCID 86618212, compound

HRID 1669522Notes

Reaction equation

HRID 1669522 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([CH2:24][NH:25][OH:26])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[C:28](OC(=O)C)(=[O:30])[CH3:29].[C:35](=[O:38])(O)[O-].[Na+].N1C=CC=C[CH:41]=1>>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([CH2:24][N:25]([O:26][C:35](=[O:38])[CH3:41])[C:28](=[O:30])[CH3:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 86618211HCID 86618211, compound

Product 1

HCID 86618212HCID 86618212, compoundYield 100%

Procedure

To a solution of {(S)-2-[4-(4-chloro-phenoxy)-phenyl]-1-hydroxyaminomethyl-ethyl}-carbamic acid tert-butyl ester (34 mg, 0.087 mmol, 1 eq.) in pyridine (2 ml) was added acetic anhydride (20 mg, 0.173 mmol, 2 eq.). And then the reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into sodium bicarbonate solution (25 ml) and extracted with ethyl acetate (3×15 ml). The combined organics was washed with 1N HCl (3×15 ml). After dried over anhydrous MgSO4, solvent was removed under reduced pressure to give a residue, which was purified by chromatography on silica gel using EA/hexane (1:2 to 1:1) as eluent to give the desired product (44 mg, 100% yield) as gummy.

Workup

  1. extractionextracted with ethyl acetate (3×15 ml)
  2. washThe combined organics was washed with 1N HCl (3×15 ml)
  3. dry with materialAfter dried over anhydrous MgSO4, solvent
  4. customwas removed under reduced pressure
  5. customto give a residue, which
  6. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a1cfe6e46b334451b6ac981ad1b38c3d
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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