Phenol → HCID 66608882, compound

HRID 1529551Notes

Reaction equation

HRID 1529551 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH3:17][C:18]([O:21][C:22]([N:24]1[CH2:31][C:30]2[O:29][C:28]([CH2:32][OH:33])=[N:27][C:26]=2[CH2:25]1)=[O:23])([CH3:20])[CH3:19].[C:34]1(O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CO>[CH3:20][C:18]([O:21][C:22]([N:24]1[CH2:31][C:30]2[O:29][C:28]([CH2:32][O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:27][C:26]=2[CH2:25]1)=[O:23])([CH3:17])[CH3:19]

Participants

7

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 66608257HCID 66608257, compound

Product 1

HCID 66608882HCID 66608882, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Di-tert-butyl azodicarboxylate (0.079 g, 0.34 mmol) was added portionwise to a stirred solution of 4,6-dihydro-2-(hydroxymethyl)-5H-pyrrolo[3,4-d]oxazole-5-carboxylic acid 1,1-dimethylethyl ester (0.055 g, 0.23 mmol), phenol (0.032 g, 0.34 mmol) and triphenylphosphine (0.090 g, 034 mmol) in THF (1 mL) at 0° C. The mixture was stirred at room temperature for 10 minutes, diluted with MeOH and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 10/90). The desired fractions were collected and evaporated in vacuo to yield 4,6-dihydro-2-(phenoxymethyl)-5H-pyrrolo[3,4-d]oxazole-5-carboxylic acid 1,1-dimethylethyl ester (0.073 g, quantitative yield) as a clear oil that was used in the next step without further purification. C17H20N2O4 LCMS: Rt 3.06, m/z 317 [M+H]+ (using method, LC-MS Method 6).

Workup

  1. customthe solvent evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 10/90)
  3. customThe desired fractions were collected
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-46e31133ba44443d8c6f9a15d3a0e8bb
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

Loading…