Lithium Hydroxide → (7-Fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid

HRID 2234772Notes

Reaction equation

HRID 2234772 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]=[C:15]([F:28])[CH:16]=3)[N:11](C(OC(C)(C)C)=O)[C:10]=2[C:9]1=[O:36])=O)(C)(C)C.[Li+].[OH-]>CO.O>[F:28][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9](=[O:36])[NH:8][CH2:21][CH:20]=[C:19]([CH2:22][C:23]([OH:25])=[O:24])[C:18]2=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 686390865-Ethoxycarbonylmethylene-7-fluoro-1-oxo-1,3,4,5-tetrahydro-azepino[3,4-b]indole-2,10-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 59789203(7-Fluoro-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

To a solution of 5-ethoxycarbonylmethylene-7-fluoro-1-oxo-1,3,4,5-tetrahydro-azepino[3,4-b]indole-2,10-dicarboxylic acid di-tert-butyl ester, (1.31 g, 2.6 mmol) in MeOH—H2O (3:1 mixture, 150 mL) is added LiOH (0.312 g, 13 mmol). The mixture is stirred at room temperature for 2 days and concentrated. Water (100 mL) is added to the residue and it is acidified with 2M NaHSO4. The precipitate is collected by filtration and dried to give (7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid; 1H NMR (DMSO-d6) δ 2.26 (d, 2H, J=5.2 Hz), 2.79 (s, 2H), 5.00 (t, 1H, 6.4 Hz), 6.22 (dt, 1H, J1=2.4 Hz, J2=10.8 Hz), 6.56 (dd, 1H, J1=4.0 Hz, J2=8.8 Hz), 6.66 (dd, 1H, J1=2.4 Hz, J2=10.8 Hz), 7.26 (t, 1H, J=5.6 Hz), 11.10 (s, 1H); m/z [M++1] 275.0.

Workup

  1. concentrationconcentrated
  2. additionWater (100 mL) is added to the residue and it
  3. filtrationThe precipitate is collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-f30af39580d0413fb54c6bf4b8bb6672
Source dataset
uspto-grants-2010_05
Patent number
US07713958B2

Reaction notes

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