Sodium Carbonate → HCID 59252507, compound

HRID 237877Notes

Reaction equation

HRID 237877 reaction equation
[CH:1]1([C:7]2[CH:28]=[CH:27][C:10]([O:11][CH2:12][CH:13]3[O:26][C:16]4=[N:17][C:18](=[O:25])[CH:19]=[C:20]([CH2:21][S:22][CH2:23][CH3:24])[N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B1([O-])OO1.[OH2:33].[OH2:34].O.O.[Na+].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(O)=O>[CH:1]1([C:7]2[CH:28]=[CH:27][C:10]([O:11][CH2:12][C@H:13]3[O:26][C:16]4=[N:17][C:18](=[O:25])[CH:19]=[C:20]([CH2:21][S:22]([CH2:23][CH3:24])(=[O:34])=[O:33])[N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 25073610HCID 25073610, compound

Product 1

HCID 59252507HCID 59252507, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(4-cyclohexyl-phenoxymethyl)-5-ethylsulfanylmethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one (0.3 g, 0.75 mmol) in HOAc (20 mL) was added sodium perborate tetrahydrate (0.3 g, 1.95 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was neutralized with sodium hydroxide (2N) to pH˜7 and further to pH˜10 with aqueous sodium carbonate. The mixture was extracted with EtOAc three times. The organic phase was washed with brine and dried (Na2SO4). Silica gel chromatography (MeOH/CH2Cl2) provided 0.254 g of the title compound. [α]D25 +5.45 (c 0.5, CHCl3).

Workup

  1. extractionThe mixture was extracted with EtOAc three times
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-2bfe37b5c74b4116877cc7d214b9a48f
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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