Carbon dioxide methanol → HCID 45380484, compound

HRID 2176147Notes

Reaction equation

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

Participants

Reactant 2

HCID 21973728Carbon dioxide methanol

HCID 45380483HCID 45380483, compound

Product 1

HCID 45380484HCID 45380484, compound

Procedure

Individual enantiomers of the racemic mixture of Example 158 (150 mg, 0.43 mmol) were separated by preparative chiral supercritical fluid chromatography (ChiralPak® OD-H 5 μm column, 21×250 mm, 35° C., 10-50% gradient of CH3OH—CO2 containing 0.1% diethylamine, flow rate 40 mL/minute) to afford the title compound as the first-eluting enantiomer: 1H NMR (500 MHz, methanol-d4) δ ppm 1.46-1.56 (m, 1H), 1.81-1.90 (m, 1H), 1.90-1.99 (m, 1H), 2.19 (s, 3H), 2.25-2.41 (m, 2H), 2.48 (s, 3H), 2.62 (dd, J=14.0, 11.6 Hz, 1H), 2.71-2.87 (m, 4H), 2.90-3.04 (m, 1H), 3.10-3.22 (m, 3H), 3.35-3.44 (m, 1H), 3.45-3.53 (m, 1H), 3.82 (dd, J=8.5, 5.2 Hz, 1H), 6.39 (d, J=7.9 Hz, 1H), 6.78 (s, 1H), 6.84 (d, J=7.6 Hz, 1H), 7.22 (d, J=7.9 Hz, 1H), 7.62 (dd, J=7.9, 2.1 Hz, 1H), 8.26 (d, J=2.1 Hz, 1H); MS (APCI) m/z 348 (M+H)+.

Sources & evidence

ORD record: ord-7d41e50cae9b494f8bae1b8d19c14ea4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09063126B2

Reaction notes

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