Diethyl Ether → HCID 57243988, compound

HRID 2294725Notes

Reaction equation

HRID 2294725 reaction equation
[CH:1]1([CH2:7][C@H:8]2[C@H:12]([C@@H:13]([CH:15]3[CH2:17][CH2:16]3)[OH:14])[O:11][C:10]([CH3:19])([CH3:18])[N:9]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.CCOCC.[OH-].[Na+]>C(Cl)Cl>[CH:1]1([CH2:7][C@H:8]2[C@H:12]([C:13]([CH:15]3[CH2:16][CH2:17]3)=[O:14])[O:11][C:10]([CH3:19])([CH3:18])[N:9]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 86751656HCID 86751656, compound

Product 1

HCID 57243988HCID 57243988, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 500 mg (1.36 mmol) of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(R)-cyclopropylhydroxymethyl)-2,2-dimethyl-3-oxazolidinecarboxylate and 750 mg (1.77 mmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one in 10 ml of methylene chloride is stirred at room temperature for 3 hours. Thereafter, 50 ml of ether and 20 ml of 2N sodium hydroxide solution are added and the mixture is stirred at room temperature for 1 hour. The organic phase is separated, washed with 20 ml of 2N sodium hydroxide solution, dried over sodium sulphate and evaporated. There are obtained 400 mg of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-(cyclopropylcarbonyl)-2,2-dimethyl-3-oxazolidinecarboxylate as a yellow oil; MS: 366 (M+H)+.

Workup

  1. stirringthe mixture is stirred at room temperature for 1 hour
  2. customThe organic phase is separated
  3. washwashed with 20 ml of 2N sodium hydroxide solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-28343675611b4268b094031e72070a16
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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