Sodium hydride → HCID 86687010, compound

HRID 1402146Notes

Reaction equation

HRID 1402146 reaction equation
[OH:1][C@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@@H:5]([N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])[CH2:4][CH2:3]1.[H-].[Na+].Cl[CH2:26][C:27]([N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)=[O:28]>C1COCC1.O>[N:29]1([C:27](=[O:28])[CH2:26][O:1][C@H:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C@@H:5]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])[CH2:4][CH2:3]2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74040Morpholine, 4-(chloroacetyl)-HCID 86687009HCID 86687009, compound

Product 1

HCID 86687010HCID 86687010, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Intermediate 32a (115 mg, 0.39 mmol) in dry THF (4 mL) was added NaH (60% in mineral oil, 23 mg, 0.59 mmol) at RT and stirred for 15 min. 4-(Chloroacetyl)morpholine (56 μL, 0.43 mmol) was then added and the mixture heated at reflux for 3.5 h. After cooling, the dark brown mixture was diluted with water and extracted with DCM. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-5% MeOH in DCM, to give the title compound as light brown foam (103 mg, 62%). LCMS (Method 3): Rt 3.44 min, m/z 443 [MNa+].

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3.5 h
  3. temperatureAfter cooling
  4. extractionextracted with DCM
  5. customThe combined organics were dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-ccc77d93f6d9465c9e2afc3480ccc33c
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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