Lithium Hydroxide → (1-Oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid

HRID 29782Notes

Reaction equation

HRID 29782 reaction equation
C(OC([N:8]1[CH2:21][CH2:20][C:19](=[CH:22][C:23]([O:25]CC)=[O:24])[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11](C(OC(C)(C)C)=O)[C:10]=2[C:9]1=[O:35])=O)(C)(C)C.[Li+].[OH-]>CO.O>[O:35]=[C:9]1[C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:20][CH2:21][NH:8]1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 686377385-Ethoxycarbonylmethylene-1-oxo-1,3,4,5-tetrahydro-azepino[3,4-b]indole-2,10-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 59789196(1-Oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 5-ethoxycarbonylmethylene-1-oxo-1,3,4,5-tetrahydro-azepino[3,4-b]indole-2,10-dicarboxylic acid di-tert-butyl ester, (0.496 g, 1.02 mmol) and LiOH (0.246 g, 10.2 mmol) in MeOH—H2O (1:1 mixture, 50 mL) is stirred at room temperature for 2 days before it is concentrated. Water is added to the residue and it is acidified with NaHSO4 (2M). The solid that is precipitated is collected by vacuum filtration and dried to yield (1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid; 1H NMR (DMSO-d6) δ 2.50 (t, 2H, J=5.6 Hz), 2.82 (s, 1H), 5.00 (t, 1H, J=6.4 Hz), 6.18 (t, 1H, J=7.2 Hz), 6.34 (t, 1H, J=7.2 Hz), 6.56 (d, 1H, J=8.8 Hz), 6.90 (d, 1H, J=8.8 Hz), 7.21 (t, 1H, J=4.4 Hz), 10.98 (s, 1H); m/z [M++1] 257.0.

Workup

  1. concentrationis concentrated
  2. additionWater is added to the residue and it
  3. customThe solid that is precipitated
  4. filtrationis collected by vacuum filtration
  5. customdried

Sources & evidence

ORD record
ord-3f458813f58d4a3f8054518374b2b61a
Source dataset
uspto-grants-2008_09
Patent number
US07423031B2

Reaction notes

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