Sodium Hydroxide → (2-tert.-Butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetic acid

HRID 2236104Notes

Reaction equation

HRID 2236104 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][C:11]2[N:12]([CH2:19][C:20]([O:22]CC)=[O:21])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][C:11]2[N:12]([CH2:19][C:20]([OH:22])=[O:21])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71063767Ethyl (2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate

Product 1

HCID 18970099(2-tert.-Butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of ethyl (2-tert.-butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate (15 mg, 0.039 mmol) in THF (0.6 ml) is treated with 0.2 N aqueous NaOH (0.29 ml, 0.058 mmol) at rt for 15 min. The reaction mixture is diluted with water (2 ml) and washed with diethyl ether (2 ml), then neutralized with conc. HCl (58 μl), and extracted with dichloromethane. The solvent is evaporated and the crude product is recrystallized from acetonitrile to afford pure compound as a yellow solid: tR (LC-1) 2.16 min; ESI-MS (positive ion): m/z 353.32 [M+Na]+ (calcd 330.38 for C18H22N2O4).

Workup

  1. washwashed with diethyl ether (2 ml)
  2. extractionextracted with dichloromethane
  3. customThe solvent is evaporated
  4. customthe crude product is recrystallized from acetonitrile
  5. customto afford pure compound as a yellow solid
  6. customtR (LC-1) 2.16 min

Sources & evidence

ORD record
ord-39c61cf51caa44d9bae0c922bafae0bc
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

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