Diethyl Ether → HCID 131733558, compound

HRID 1747230Notes

Reaction equation

HRID 1747230 reaction equation
[Li]C.[CH3:3]COCC.[C:8]([O:12][C:13]([N:15]1[C@H:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N:28]3[N:32]=[CH:31][CH:30]=[N:29]3)[CH:23]=2)[CH2:19][O:18][CH2:17][C:16]1=[O:33])=[O:14])([CH3:11])([CH3:10])[CH3:9]>C1COCC1>[C:8]([O:12][C:13](=[O:14])[NH:15][C@H:20]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:28]2[N:29]=[CH:30][CH:31]=[N:32]2)[CH:23]=1)[CH2:19][O:18][CH2:17][C:16](=[O:33])[CH3:3])([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 118117798HCID 118117798, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 131733558HCID 131733558, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeLi 1.6 M in Et2O (3.6 mL, 5.82 mmol) was added dropwise to a −78° C. solution of (R)-3-oxo-5-(3-[1,2,3]triazol-2-yl-benzyl)-morpholine-4-carboxylic acid tert-butyl ester I-5 (1.49 g, 4.16 mmol) in THF (15 mL) and the resulting mixture was stirred at −78° C. for 3 h. The reaction mixture was quenched with sat. aq. NH4Cl, warmed to RT and the solvent was removed in vacuo. The remaining aqueous layer was extracted with EtOAc (3×) and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. The crude product was purified by flash chromatography (eluting with 20% to 50% EtOAc in hexane) to give the title compound as a yellow solid. LC-MS B: tR=0.81 min; [M+H-Boc]+=259.17.

Workup

  1. customThe reaction mixture was quenched with sat. aq. NH4Cl
  2. customthe solvent was removed in vacuo
  3. extractionThe remaining aqueous layer was extracted with EtOAc (3×)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude product was purified by flash chromatography (eluting with 20% to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-85ba3a6f65a847ae9ef7a0ab370ceced
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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