Methanol → HCID 71087901, compound

HRID 927797Notes

Reaction equation

HRID 927797 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]([CH3:16])([C:10]1[NH:14][C:13](=[O:15])[O:12][N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].CO.[C:20]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]([CH3:9])([C:10]1[N:14]([CH3:20])[C:13](=[O:15])[O:12][N:11]=1)[CH3:16])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 136413187HCID 136413187, compound

Product 1

HCID 71087901HCID 71087901, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

To a colorless solution of [1-methyl-1-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-ethyl]-carbamic acid tert-butyl ester (1.5 g, 6.17 mmol) in THF (30.0 mL) was added methanol (296 mg, 374 μl, 9.25 mmol) and triphenylphosphine (1.94 g, 7.4 mmol). The mixture was cooled to 0-5° C. and diisopropyl azodicarboxylate (1.5 g, 1.46 ml, 7.4 mmol) was added slowly over a period of 20 minutes at max: 5° C. The mixture was stirred for another 30 minutes at 0-5° C. and for 16 hours at room temperature. Solvents were removed in vacuo and the residue was purified by flash chromatography (silica gel, 70 g, 0% to 100% ethyl acetate in heptane) to give the title compound (1.4 g, 89%) as white solid; GC-MS (EI) 98%, 257.0 (M)+.

Workup

  1. custom5° C
  2. customSolvents were removed in vacuo
  3. customthe residue was purified by flash chromatography (silica gel, 70 g, 0% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b5d202f4eb184692ab96549151713033
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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