Lithium iodide → HCID 66874287, compound

HRID 249926Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of methyl 2-((2S,6S)-2,6-dimethyl-4-(pyrrolidine-1-carbonyl)piperazin-1-yl)benzoxazole-4-carboxylate (200 mg, 0.52 mmol) in pyridine (2 mL) was added lithium iodide (550 mg, 4.11 mmol). The mixture was heated at 110° C. for 18 h and allowed to cool to ambient temperature before partitioning with 9:1 mixture of dichloromethane and isopropanol (100 mL) and 1 N HCl (50 mL). The non-homogenous organic layer was washed with brine and concentrated under reduced pressure. The residue was treated with 9:1 toluene/methanol (100 mL) and concentrated in vacuo to afford crude 2-((2S,6S)-2,6-dimethyl-4-(pyrrolidine-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 mixture of dichloromethane and isopropanol (100 mL) and 1 N HCl (50 mL)
washThe non-homogenous organic layer was washed with brine
concentrationconcentrated under reduced pressure
additionThe residue was treated with 9:1 toluene/methanol (100 mL)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c2853798a58f445f90930b6d113d8ed5
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863271B2

Reaction notes

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