Sodium periodate → HCID 90219100, compound

HRID 1486158Notes

Reaction equation

HRID 1486158 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:15][C@@H:14]([CH2:16][CH2:17][OH:18])[CH2:13][CH2:12][C@@H:11]1[CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:29].[Na+]>C(#N)C.C(Cl)(Cl)(Cl)Cl.O.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]1[C@@H:11]([CH2:19][NH:20][C:21]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:27])[CH2:12][CH2:13][C@H:14]([CH2:16][C:17]([OH:29])=[O:18])[CH2:15]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 90218975HCID 90218975, compound

Product 1

HCID 90219100HCID 90219100, compoundYield 49.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (racemic)-tert-butyl N-[[(1S,2S,4S)-2-[(tert-butoxycarbonylamino)methyl]-4-(2-hydroxyethyl)cyclohexyl]methyl]carbamate (772 mg, 2 mmol) in acetonitrile (3 mL), carbon tetrachloride (3 mL) and water (4.5 mL) is added sodium periodate (1.28 g, 6 mmol) followed by RuCl3.H2O (21 mg, 0.1 mmol). The resulting mixture is stirred for 2 hr then diluted with EtOAc, washed with brine, dried over MgSO4 and concentrated. The residue is taken up in saturated sodium carbonate solution and extracted with EtOAc. The aqueous phase is acidified with HCl (2M aqueous) and extracted with EtOAc. The organic extract is washed with brine, dried over MgSO4 and concentrated. This residue is purified by silica chromatography (eluting with ethyl acetate) to give the title compound (394 mg) as a viscous oil. 1H NMR (DMSO-d6) δ 0.7-1.0 (m, 1H), 1.0-1.9 (m, 9H), 1.39 (s, 18H), 2.0-2.3 (m, 2H), 2.6-3.18 (m, 4H), 6.6-6.8 (bm, 2H).

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. extractionextracted with EtOAc
  5. extractionextracted with EtOAc
  6. extractionThe organic extract
  7. washis washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThis residue is purified by silica chromatography (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-4ab5910062a14221831ed09ffce0e8f9
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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