Trifluoroacetic acid → HCID 17842376, compound

HRID 546403Notes

Reaction equation

HRID 546403 reaction equation
FC(F)(F)C(O)=O.C(O[C:13]([N:15]1[CH2:20][CH2:19][C:18]2[N:21]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[O:23][C:17]=2[CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:27][O:26][C:24]([C:22]1[O:23][C:17]2[CH2:16][N:15]([CH3:13])[CH2:20][CH2:19][C:18]=2[N:21]=1)=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178424645-tert-Butyl 2-methyl 6,7-dihydro[1,3]oxazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate

Product 1

HCID 17842376HCID 17842376, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (15 ml) was added to a solution of 5-(tert-butoxycarbonyl)-2-methoxycarbonyl-4,5,6,7-tetrahydrooxazolo[5,4-c]pyridine (500 mg) in dichloromethane (15 ml) at room temperature, and the mixture was stirred for 10 minutes. The reaction mixture was concentrated under reduced pressure, and dichloromethane (20 ml), triethylamine (0.495 ml), acetic acid (205 ml), formalin (0.230 ml) and sodium triacetoxyborohydride (570 mg) were added to the resultant residue at room temperature. After stirring for 15 minutes, dichloromethane (20 ml) and a saturated aqueous solution (50 ml) of sodium hydrogencarbonate were added to separate an organic layer. The water layer was extracted with dichloromethane (3×20 ml). After the resultant organic layers were combined and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=20:1→10:1) to obtain the title compound (257 mg) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and dichloromethane (20 ml), triethylamine (0.495 ml), acetic acid (205 ml), formalin (0.230 ml) and sodium triacetoxyborohydride (570 mg)
  2. additionwere added to the resultant residue at room temperature
  3. stirringAfter stirring for 15 minutes
  4. additiondichloromethane (20 ml) and a saturated aqueous solution (50 ml) of sodium hydrogencarbonate were added
  5. customto separate an organic layer
  6. extractionThe water layer was extracted with dichloromethane (3×20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1→10:1)

Sources & evidence

ORD record
ord-4145b16db8784cfaba2692a6d2156689
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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