Sodium Iodide → HCID 67032496, compound

HRID 920588Notes

Reaction equation

HRID 920588 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-].[CH2:31](Cl)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CC#N.C1COCC1.CC#N>[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:19][CH:20]=2)[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 10796Cesium carbonateHCID 666540623-[2-(4-Hydroxy-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester

Product 1

HCID 67032496HCID 67032496, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

A mixture of 3-[2-(4-hydroxy-phenyl)-morpholin-4-yl]-propionic acid tert-butyl ester) (76.8 mg; 0.25 mmol), Cs2CO3 (241 mg; 0.74 mmol), and NaI (3.7 mg, 25 μmol) in CH3CN/THF (6:4; 2.5 mL) was stirred for three hours at RT. Subsequently, benzyl chloride (35 μL; 0.3 mmol) in CH3CN (1 mL) was added and the resulting mixture was heated at 60° C., for 20 h. After cooling to RT the solvents were removed in vacuo. The residue was partitioned between CH2Cl2 and 1M aqueous K2CO3. The layers were separated and the aqueous layer washed with CH2Cl2. The combined organic layers were concentrated in vacuo, and the residue dried under vacuum, at 40° C., overnight. The obtained product was used as such in the next step.

Workup

  1. temperaturethe resulting mixture was heated at 60° C., for 20 h
  2. temperatureAfter cooling to RT the solvents
  3. customwere removed in vacuo
  4. customThe residue was partitioned between CH2Cl2 and 1M aqueous K2CO3
  5. customThe layers were separated
  6. washthe aqueous layer washed with CH2Cl2
  7. concentrationThe combined organic layers were concentrated in vacuo
  8. customthe residue dried under vacuum, at 40° C., overnight

Sources & evidence

ORD record
ord-9309d6dcff8e496fb1f97170661f8caf
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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