Sodium Hydroxide → HCID 67344080, compound

HRID 1669489Notes

Reaction equation

HRID 1669489 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]([CH3:52])[S:11]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH:23]2[CH2:30][N:29]3[C:31]4[CH:32]=[C:33]([C:44]([O:46]C)=[O:45])[CH:34]=[CH:35][C:36]=4[C:37]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)=[C:28]3[C:27]3[CH:48]=[CH:49][CH:50]=[CH:51][C:26]=3[O:25][CH2:24]2)[CH2:16][CH2:15]1)(=[O:13])=[O:12])=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8]([N:10]([CH3:52])[S:11]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH:23]2[CH2:30][N:29]3[C:31]4[CH:32]=[C:33]([C:44]([OH:46])=[O:45])[CH:34]=[CH:35][C:36]=4[C:37]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)=[C:28]3[C:27]3[CH:48]=[CH:49][CH:50]=[CH:51][C:26]=3[O:25][CH2:24]2)[CH2:16][CH2:15]1)(=[O:13])=[O:12])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67343811HCID 67343811, compound

Product 1

HCID 67344080HCID 67344080, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

2N NaOH (aq) (30 eq) was added to a solution of methyl 7-[3-(4-{[(tert-butoxycarbonyl)(methyl)amino]sulfonyl}piperazin-1-yl)propyl]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.06 M) in MeOH and the reaction stirred at 70° C. for 3 h. The reaction was allowed to cool to RT before reducing the volume of MeOH 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 brine before being dried (Na2SO4), filtered and concentrated in vacuo. The material was taken on without further purification. (ES+) m/z 681 (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 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-5004506e5a5247aaa9db383781034665
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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