Phenol → HCID 66609159, compound

HRID 1529546Notes

Reaction equation

HRID 1529546 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH2:17]([O:19][C:20]([N:22]1[CH2:27][CH2:26][C:25]2[N:28]=[C:29]([CH2:31][OH:32])[O:30][C:24]=2[CH2:23]1)=[O:21])[CH3:18].[C:33]1(O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:17]([O:19][C:20]([N:22]1[CH2:27][CH2:26][C:25]2[N:28]=[C:29]([CH2:31][O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:30][C:24]=2[CH2:23]1)=[O:21])[CH3:18]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 66609140HCID 66609140, compound

Product 1

HCID 66609159HCID 66609159, compoundYield 114.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Di-tert-butyl azodicarboxylate (2.20 g, 9.5 mmol) was added portionwise to a stirred solution of 6,7-dihydro-2-(hydroxymethyl)-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (1.80 g, 7.95 mmol), phenol (0.90 g, 9.5 mmol) and triphenylphosphine (2.5 g, 9.5 mmol) in THF (40 mL) at 0° C. The mixture was stirred at room temperature for 20 minutes. The solvent was evaporated in vacuo and the crude product purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80). The desired fractions were collected and evaporated in vacuo. The crude product was dissolved with AcOEt and washed with a 10% solution of NaOH. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 6,7-dihydro-2-(phenoxymethyl)-oxazolo[5,4-c]pyridine-5(4H)-carboxylic acid ethyl ester (2.75 g, quantitative yield) that was used in the next step without further purification. C16H18N2O4 LCMS: Rt 2.43, m/z 303 [M+H]+ (using method, LC-MS Method 6).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude product purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80)
  3. customThe desired fractions were collected
  4. customevaporated in vacuo
  5. dissolutionThe crude product was dissolved with AcOEt
  6. washwashed with a 10% solution of NaOH
  7. customThe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-56185e5d7d4347dc96fceb6c4b42b09a
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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