Sodium Hydroxide → (7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

HRID 1669396Notes

Reaction equation

HRID 1669396 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][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]C)=[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:9])([CH3:6])([CH3:5])[CH3:4]>CO.C1COCC1>[C:3]([O:7][C:8]([NH:10][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]([OH:37])=[O:36])[CH:25]=[CH:26][C:27]=3[C:28]([CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[C:19]2[C:18]2[CH:39]=[CH:40][CH:41]=[CH:42][C:17]=2[O:16][CH2:15]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53381224methyl(7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 66674687(7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

2N NaOH (aq) (6 eq) was added to a solution of methyl (7R)-7-[{2-[(tert-butoxycarbonyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.02 M) in MeOH/THF (3/1) and the reaction stirred vigorously at 60° C. for 4 h. The reaction was allowed to cool to RT before reducing the volume of MeOH/THF in vacuo. The residue was partitioned between 1N HCl (aq) and EtOAc, ensuring the aqueous phase was acidic. The aqueous was extracted a second time with EtOAc and the combined organics washed with water, brine before being dried (Na2SO4), filtered and concentrated in vacuo. The material was taken on without further purification. MS (ES+) m/z 548 (M+H)+.

Workup

  1. temperatureto cool to RT
  2. customThe residue was partitioned between 1N HCl (aq) and EtOAc
  3. extractionThe aqueous was extracted a second time with EtOAc
  4. washthe combined organics washed with water, brine
  5. dry with materialbefore being dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe material was taken on without further purification

Sources & evidence

ORD record
ord-204a6783fbc34bb287d0d9ee4810c7db
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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