Water → HCID 66820273, compound

HRID 1044775Notes

Reaction equation

HRID 1044775 reaction equation
[N:1]([CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[N:9]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[CH3:15][C:10]1([C:8]2[N:9]=[C:5]([CH2:4][NH2:1])[O:6][CH:7]=2)[O:14][CH2:13][CH2:12][O:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 90752751HCID 90752751, compound

Product 1

HCID 66820273HCID 66820273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (4-(2-methyl-[1,3]dioxolan-2-yl)-oxazol-2-yl)-methanol (230 mg, 1.24 mmol) in dry CH2Cl2 (10 mL) was treated at 0° C. with Et3N (0.23 mL, 1.64 mmol) followed by DMAP (15 mg, 0.12 mmol) and Ms-Cl (0.13 mL, 1.61 mmol). After stirring at 0° C. for 1 h, the reaction was quenched with water (10 mL). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give crude (4-(2-methyl-[1,3]dioxolan-2-yl)oxazol-2-yl)methyl methanesulfonate as a colorless oil. The crude material was dissolved in dry DMF (6 mL) and treated with NaN3 (93 mg, 1.41 mmol) at 80° C. until completion of the reaction. The reaction mixture was then cooled down to rt and partitioned between EA and water. The layers were separated and the org. layer dried over MgSO4, filtered and concentrated under reduced pressure to give crude 2-(azidomethyl)-4-(2-methyl-[1,3]dioxolan-2-yl)oxazole as a colorless oil. To a solution of the crude azide in THF (9 mL) were added polymer-supported Ph3P (1.4 eq.) and water (3 mL). The reaction mixture was stirred at 55° C. until completion of the reaction, cooled down to rt and filtered. The filtrate was partitioned between EA and aq. sat. NaHCO3 and the layers separated. The aq. layer was concentrated under reduced pressure, the residue triturated in EtOH and the solid filtered off. The filtrate was dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound as an orange oil. LC-MS-conditions 01: tR=0.22 min; [M+H]+=185.00.

Workup

  1. temperaturecooled down to rt
  2. filtrationfiltered
  3. customThe filtrate was partitioned between EA and aq. sat. NaHCO3
  4. customthe layers separated
  5. concentrationThe aq. layer was concentrated under reduced pressure
  6. customthe residue triturated in EtOH
  7. filtrationthe solid filtered off
  8. dry with materialThe filtrate was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7ee6c634d8a469cb7583f216fcffc7b
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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