Sodium hydride → HCID 86687010, compound

HRID 2282422Notes

Reaction equation

HRID 2282422 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-03b1287949f14b90aeef7a721844340a
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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