Sodium Hydroxide → (7S)-7-{2-[{3-[(benzylamino)sulfonyl]propyl}(methyl)amino]ethoxy}-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

HRID 421955Notes

Reaction equation

HRID 421955 reaction equation
[OH-].[Na+].[CH2:3]([NH:10][S:11]([CH2:14][CH2:15][CH2:16][N:17]([CH3:50])[CH2:18][CH2:19][O:20][C@H:21]1[CH2:28][N:27]2[C:29]3[CH:30]=[C:31]([C:42]([O:44]C)=[O:43])[CH:32]=[CH:33][C:34]=3[C:35]([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[C:26]2[C:25]2[CH:46]=[CH:47][CH:48]=[CH:49][C:24]=2[O:23][CH2:22]1)(=[O:13])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([NH:10][S:11]([CH2:14][CH2:15][CH2:16][N:17]([CH3:50])[CH2:18][CH2:19][O:20][C@H:21]1[CH2:28][N:27]2[C:29]3[CH:30]=[C:31]([C:42]([OH:44])=[O:43])[CH:32]=[CH:33][C:34]=3[C:35]([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[C:26]2[C:25]2[CH:46]=[CH:47][CH:48]=[CH:49][C:24]=2[O:23][CH2:22]1)(=[O:13])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 66674408methyl(7S)-7-{2-[{3-[(benzylamino)sulfonyl]propyl}(methyl)amino]ethoxyl}-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 66674839(7S)-7-{2-[{3-[(benzylamino)sulfonyl]propyl}(methyl)amino]ethoxy}-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydroxide (2 N, 6 eq.) was added to a solution of methyl(7S)-7-{2-[{3-[(benzylamino)sulfonyl]propyl}(methyl)amino]ethoxy}-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.025 M) in MeOH. The reaction was heated at 60° C. for 1 h prior to introducing further sodium hydroxide (2 N, 10 eq.) and continuing heating for 2 h. The mixture was then partitioned between H2O and EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The product was used in the next step without further purification. (ES+) m/z 660 (M+H)+.

Workup

  1. temperaturecontinuing heating for 2 h
  2. customThe mixture was then partitioned between H2O and EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-4e77d51c14264909ad3004c5ba1faada
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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