Ethanol hexane → HCID 86641353, compound

HRID 1693327Notes

Reaction equation

HRID 1693327 reaction equation
[CH:1]1([N:4]([C:44](=[O:49])[C:45]([F:48])([F:47])[F:46])[CH:5]2[C:14]3[CH2:13][S:12][N:11]=[C:10]([N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]4=[N:30][N:31]([CH2:33][C:34]5[C:39]([CH3:40])=[C:38]([O:41][CH3:42])[C:37]([CH3:43])=[CH:36][N:35]=5)[N:32]=[C:7]([C:8]=34)[CH2:6]2)[CH2:3][CH2:2]1.C(O)C.CCCCCC>C(O)C>[CH:1]1([N:4]([C:44](=[O:49])[C:45]([F:46])([F:48])[F:47])[C@@H:5]2[C:14]3[CH2:13][S:12][N:11]=[C:10]([N:15]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:9]4=[N:30][N:31]([CH2:33][C:34]5[C:39]([CH3:40])=[C:38]([O:41][CH3:42])[C:37]([CH3:43])=[CH:36][N:35]=5)[N:32]=[C:7]([C:8]=34)[CH2:6]2)[CH2:3][CH2:2]1.[CH:1]1([N:4]([C:44](=[O:49])[C:45]([F:46])([F:48])[F:47])[C@H:5]2[C:14]3[CH2:13][S:12][N:11]=[C:10]([N:15]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:9]4=[N:30][N:31]([CH2:33][C:34]5[C:39]([CH3:40])=[C:38]([O:41][CH3:42])[C:37]([CH3:43])=[CH:36][N:35]=5)[N:32]=[C:7]([C:8]=34)[CH2:6]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 21879635Ethanol hexaneHCID 86641352HCID 86641352, compound

Product 2

HCID 86641353HCID 86641353, compoundYield 43%HCID 86641354HCID 86641354, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Di-tert-butyl {8-[cyclopropyl(trifluoroacetyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate (1.0 g) was dissolved in ethanol (20 ml) and optically resolved by AD column 50×500 mm (15% ethanol/n-hexane 50.0 ml/min). This operation was repeated three times to obtain di-tert-butyl {8-(S)-[cyclopropyl(trifluoroacetyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate (RT=70 min) (1.3 g, 43%) and di-tert-butyl {8-(R)-[cyclopropyl(trifluoroacetyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate (RT=130 min) (1.0 g, 33%).

Sources & evidence

ORD record
ord-851afb0ded6340dfa4adc4923b1d8122
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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