HCID 72347756, compound → HCID 59650935, compound

HRID 552892Notes

Reaction equation

HRID 552892 reaction equation
[CH3:1][C:2]1([NH:30]C(=O)OC(C)(C)C)[CH2:20][C:19]2[CH:21]=[C:15]([CH:16]=[CH:17][CH:18]=2)[CH2:14][CH:13]=[CH:12][CH2:11][C:10]2=[CH:22][C:6](=[CH:7][C:8]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])=[N:9]2)[CH2:5][O:4][C:3]1=[O:29]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:30][C:2]1([CH3:1])[CH2:20][C:19]2[CH:21]=[C:15]([CH:16]=[CH:17][CH:18]=2)[CH2:14][CH:13]=[CH:12][CH2:11][C:10]2=[CH:22][C:6](=[CH:7][C:8]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])=[N:9]2)[CH2:5][O:4][C:3]1=[O:29].[NH2:30][C:2]1([CH3:1])[CH2:20][C:19]2[CH:21]=[C:15]([CH:16]=[CH:17][CH:18]=2)[CH2:14][CH:13]=[CH:12][CH2:11][C:10]2=[CH:22][C:6](=[CH:7][C:8]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])=[N:9]2)[CH2:5][O:4][C:3]1=[O:29]

Participants

5

Reactant 1

HCID 72347756HCID 72347756, compound

Product 2

HCID 59650935HCID 59650935, compoundHCID 67170621HCID 67170621, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl [(3EZ)-14-methyl-8-[methyl(methylsulfonyl)amino]-13-oxo-12-oxa-7-azatricyclo[14.3.1.16,10]henicosa-1(20),3,6(21),7,9,16,18-heptaen-14-yl]carbamate (14 mg, 0.026 mmol) (Intermediate V.11.c.1) in DCM (0.5 mL) and TFA (1.5 mL) was stirred at rt for 1 h. Concentration, purification and separation of EZ isomers by reverse phase preparative HPLC (5-95% CH3CN in water containing 0.1% TFA) gave N-[(3E)-14-Amino-14-methyl-13-oxo-12-oxa-7-azatricyclo[14.3.1.16,10]henicosa-1(20),3,6(21),7,9,16,18-heptaen-8-yl]-N-methylmethanesulfonamide and N-[(3Z)-14-Amino-14-methyl-13-oxo-12-oxa-7-azatricyclo[14.3.1.16,10]henicosa-1(20),3,6(21),7,9,16,18-heptaen-8-yl]-N-methylmethanesulfonamide

Workup

  1. concentrationConcentration, purification and separation of EZ isomers by reverse phase preparative HPLC (5-95% CH3CN in water containing 0.1% TFA)

Sources & evidence

ORD record
ord-b6a17c6c46df442693f458cf7ca986e6
Source dataset
uspto-grants-2011_05
Patent number
US07951949B2

Reaction notes

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