Lithium iodide → HCID 66873722, compound

HRID 249927Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])[CH2:5][C@H:4]([CH3:16])[N:3]1[C:17]1[O:18][C:19]2[C:20](=[C:22]([C:26]([O:28]C)=[O:27])[CH:23]=[CH:24][CH:25]=2)[N:21]=1.[I-].[Li+]>N1C=CC=CC=1>[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)=[O:9])[CH2:5][C@H:4]([CH3:16])[N:3]1[C:17]1[O:18][C:19]2[C:20](=[C:22]([C:26]([OH:28])=[O:27])[CH:23]=[CH:24][CH:25]=2)[N:21]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of methyl 2-((2S,6S)-2,6-dimethyl-4-(piperidine-1-carbonyl)piperazin-1-yl)benzoxazole-4-carboxylate (200 mg, 0.52 mmol) in pyridine (2 mL) was added lithium iodide (495 mg, 3.70 mmol). The mixture was heated at 110° C. for 18 h and allowed to cool to ambient temperature before partitioning with 9:1 dichloromethane/2-propanol (100 mL) and 1 N HCl (50 mL). The non-homogenous organic layer was washed with brine and concentrated in vacuo. The residue was treated with 9:1 mixture of toluene and methanol (100 mL) and concentrated under reduced pressure to afford crude 2-((2S,6S)-2,6-dimethyl-4-(piperidine-1-carbonyl)piperazin-1-yl)benzoxazole-4-carboxylic acid as a brown solid which was directly elaborated without purification.

Workup

temperatureto cool to ambient temperature
custombefore partitioning with 9:1 dichloromethane/2-propanol (100 mL) and 1 N HCl (50 mL)
washThe non-homogenous organic layer was washed with brine
concentrationconcentrated in vacuo
additionThe residue was treated with 9:1 mixture of toluene and methanol (100 mL)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-420f2568c4ca42d8a3d0a3754fb39e52
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863271B2

Reaction notes

Loading…