Sodium Hydroxide → HCID 67358360, compound

HRID 1664495Notes

Reaction equation

HRID 1664495 reaction equation
[CH2:1]([N:8]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:9]([CH:11]1[CH2:23][C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH2:24][C:25]([O:27]CC)=[O:26])[C:14]=2[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH2:30]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([CH:11]1[CH2:23][C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([CH2:24][C:25]([OH:27])=[O:26])[C:14]=2[CH2:13][CH2:12]1)=[O:10])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86635307HCID 86635307, compound

Product 1

HCID 67358360HCID 67358360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of crude ethyl (±)-(3-dibenzylcarbamoyl-1,2,3,4-tetrahydro-carbazol-9-yl)-acetate (0.1 mmol) in THF (1 ml) is treated with 0.2 N aqueous NaOH (0.5 ml, 0.1 mmol) added at rt for 15 min. Then, the reaction mixture is extracted twice with diethyl ether (2 ml), acidified to pH 1 by addition of 1M HCl and extracted with CH2Cl2. The combined organic layers are dried (Na2SO4), filtered and evaporated. The resulting solid is recrystallized from diethyl ether to yield title compound as a pale yellow solid. tR (LC-2) 2.74 min; MS (positive ion) m/z 453.26 [M+H]+ (calcd 452.55 for C29H28N2O3).

Workup

  1. additionadded at rt for 15 min
  2. extractionThen, the reaction mixture is extracted twice with diethyl ether (2 ml)
  3. additionacidified to pH 1 by addition of 1M HCl
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic layers are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-4c4cea2936224ae7b442a40a159bed32
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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