Lithium iodide → HCID 66874469, compound

HRID 249923Notes

Reaction equation

HRID 249923 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8](=[O:12])[N:9]([CH3:11])[CH3:10])[CH2:5][C@H:4]([CH3:13])[N:3]1[C:14]1[O:15][C:16]2[C:17](=[C:19]([C:23]([O:25]C)=[O:24])[CH:20]=[CH:21][CH:22]=2)[N:18]=1.[Li+].[I-]>N1C=CC=CC=1>[CH3:1][C@H:2]1[CH2:7][N:6]([C:8](=[O:12])[N:9]([CH3:11])[CH3:10])[CH2:5][C@H:4]([CH3:13])[N:3]1[C:14]1[O:15][C:16]2[C:17](=[C:19]([C:23]([OH:25])=[O:24])[CH:20]=[CH:21][CH:22]=2)[N:18]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 66874035HCID 66874035, compound

Product 1

HCID 66874469HCID 66874469, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of methyl 2-((2S,6S)-2,6-dimethyl-4-(dimethylcarbamoyl)piperazin-1-yl)benzoxazole-4-carboxylate (265 mg, 0.74 mmol) in pyridine (5 mL) was added LiI (984 mg, 7.35 mmol). The mixture was heated at 110° C. for 14 h and allowed to cool to ambient temperature. The reaction was partially concentrated under reduced pressure before partitioning with 9:1 CH2Cl2/2-propanol (50 mL) and 1 N HCl (20 mL). The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford crude 2-((2S,6S)-2,6-dimethyl-4-(dimethylcarbamoyl)piperazin-1-yl)benzoxazole-4-carboxylic acid as an orange oil which was directly elaborated without purification.

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationThe reaction was partially concentrated under reduced pressure
  3. custombefore partitioning with 9:1 CH2Cl2/2-propanol (50 mL) and 1 N HCl (20 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5e1c6a93d9f426da840db2658819d89
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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