Dimethyl Sulfide → methyl (7R)-7-[{2-[[4-(aminosulfonyl)butyl](methyl)amino]ethyl}(methyl)amino]-1 4-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 421947Notes

Reaction equation

HRID 421947 reaction equation
[NH2:1][S:2]([CH2:5][CH2:6][CH2:7][C:8]([N:10]([CH3:44])[CH2:11][CH2:12][N:13]([CH3:43])[C@@H:14]1[CH2:21][N:20]2[C:22]3[CH:23]=[C:24]([C:35]([O:37][CH3:38])=[O:36])[CH:25]=[CH:26][C:27]=3[C:28]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[C:19]2[C:18]2[CH:39]=[CH:40][CH:41]=[CH:42][C:17]=2[O:16][CH2:15]1)=O)(=[O:4])=[O:3].CSC>C1COCC1>[NH2:1][S:2]([CH2:5][CH2:6][CH2:7][CH2:8][N:10]([CH3:44])[CH2:11][CH2:12][N:13]([CH3:43])[C@@H:14]1[CH2:21][N:20]2[C:22]3[CH:23]=[C:24]([C:35]([O:37][CH3:38])=[O:36])[CH:25]=[CH:26][C:27]=3[C:28]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[C:19]2[C:18]2[CH:39]=[CH:40][CH:41]=[CH:42][C:17]=2[O:16][CH2:15]1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 66674679methyl(7R)-7-[{2-[[4-(aminosulfonyl)butanoyl](methyl)amino]ethyl}(methyl)-amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 66675081methyl (7R)-7-[{2-[[4-(aminosulfonyl)butyl](methyl)amino]ethyl}(methyl)amino]-1 4-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl(7R)-7-[{2-[[4-(aminosulfonyl)butanoyl](methyl)amino]ethyl}-(methyl)amino]-14-cyclohexyl-7,8-dihydro -6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.03 M) in THF was treated with BH3.DMS complex (2 M in THF; 15 eq.). The resulting solution was stirred at RT for 1 h. The reaction was quenched by the careful addition of HCl/MeOH (1.25 M) and the resulting solution heated at 80° C. until all volatiles had evaporated to afford the title compound. The product was used in the next step without further purification. (ES+) m/z 611 (M+H)+.

Workup

  1. customThe reaction was quenched by the careful addition of HCl/MeOH (1.25 M)
  2. temperaturethe resulting solution heated at 80° C. until all volatiles
  3. customhad evaporated

Sources & evidence

ORD record
ord-432ae404119640778f3fa958fda5477e
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

Loading…