Methanol → Carbon Dioxide

HRID 554712Notes

Reaction equation

HRID 554712 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])=[N:6][CH:7]=1.C[OH:25]>>[C:8](=[O:9])=[O:25].[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:12]([Cl:14])([Cl:13])[Cl:15])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 44623928HCID 44623928, compound

Product 2

HCID 280Carbon DioxideHCID 44623928HCID 44623928, compound

Procedure

Compound 34 has identical NMR as Compound 29, but has an (−) optical rotation. Compound 34 was obtained from chiral HPLC separation (Chiralpak IA 30% MeOH, CO2 at 100 barr) of Compound 29 above: and collect the first eluting peak (−) enantiomer: [α]=−121° (c 0.69 in CHCl3). 1H NMR (300 MHz, CDCl3) δ 8.62-8.61 (m, 1H), 8.50 (d, J=9.9 Hz, 1H), 8.12 (dd, J=8.4, 0.6 Hz, 1H), 8.04-8.00 (m, 1H), 7.18 (d, J=9.0 Hz, 2H), 6.78 (d, J=8.0 Hz, 2H), 6.28 (t, J=9.6 Hz, 1H), 4.55 (d, J=9.6 Hz, 1H).

Sources & evidence

ORD record
ord-adcf5251fcee439986e09782aa2d7b23
Source dataset
uspto-grants-2011_11
Patent number
US08049037B2

Reaction notes

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