Triacetoxyperiodinane → HCID 67189447, compound

HRID 2355435Notes

Reaction equation

HRID 2355435 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:18][N:19]([CH3:29])[C:20]([O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])[C@@H:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCCl.CCOCC>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:18][N:19]([CH3:29])[C:20]([O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])=[O:21])[C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67191992HCID 67191992, compound

Product 1

HCID 67189447HCID 67189447, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (1R,2R)-2-(t-butoxycarbonylamino)-1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-1-ol (0.76 g, 1.76 mmol) in 1,2-dichloroethane (4 mL) was added Dess-Martin periodinane (1.05 g, 2.29 mmol), and the resulting mixture was heated in a CEM microwave reactor at 70° C. for 3 min. Completion of reaction was confirmed by TLC. The mixture was diluted with ether (20 mL), washed with 1 N aq NaOH (2×10 mL) and brine, dried over Na2SO4, and concentrated to give crude (R)-2-(t-butoxycarbonylamino)-1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-1-one (0.74 g), which was used without purification.

Workup

  1. customCompletion of reaction
  2. washwashed with 1 N aq NaOH (2×10 mL) and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7877f07191b0469aaba6d96d04bd95f8
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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