Lithium Hydroxide → HCID 9799156, compound

HRID 1373145Notes

Reaction equation

HRID 1373145 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[C:7]2[C:8]3[CH:24]([C:25](=[O:27])[NH2:26])[CH2:23][CH2:22][C:9]=3[N:10]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]=2[CH:12]=[CH:13][CH:14]=1.[Li+].[OH-]>C1COCC1.CO>[CH2:15]([N:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:6]([O:5][CH2:4][C:3]([OH:28])=[O:2])[C:7]=2[C:8]2[CH:24]([C:25](=[O:27])[NH2:26])[CH2:23][CH2:22][C:9]1=2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 9969904HCID 9969904, compound

Product 1

HCID 9799156HCID 9799156, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of (4-Benzyl-1-carbamoyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-8-yloxy)-acetic acid methyl ester (24 mg; 0.06 mmol) in THF (2 mL) and MeOH (0.7 mL) was treated with 1N aqueous LiOH (0.1 mL). The mixture was stirred for 14 hrs and was concentrated in vacuo. Purification by reverse phase chromatography (Vydac C18column; 5% to 70% of 0.1% HCl/H2O in 0.1% HCl/CH3CN) afforded 21 mg (92%) (4-Benzyl-1-carbamoyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-8-yloxy)-acetic acid, compound 8, Scheme 1, as a white solid. 1H NMR (CDCl3) δ 7.30–7.19 (m, 4H), 7.09 (d, J=7.3 Hz, 2H), 6.98 (d, J=8.8 Hz, 1H), 6.87 (app t, J=7.8 Hz, 1H), 6.67 (br s, 1H), 6.42 (d, J=7.8 Hz, 1H), 5.25 (s, 2H), 4.66–4.51 (m, 2H), 3.85 (d, 7.8 Hz, 1H), 2.96–2.84 (m, 1H), 2.76–2.62 (m, 3H); IR (KBr) 3413, 1716, 1667, 1636, 1614, 1496, 1432, 1256, 1115, 721, 701 cm−1; FDMS, 365 (M+1); Anal calcd for C21H20N2O4.0.5 HCl: C, 64.92; H, 5.40; N, 7.32. Found: C, 64.75; H,5.65; N, 7.13.

Workup

  1. concentrationwas concentrated in vacuo
  2. customPurification by reverse phase chromatography (Vydac C18column; 5% to 70% of 0.1% HCl/H2O in 0.1% HCl/CH3CN)

Sources & evidence

ORD record
ord-514d0324d241463280ca7394e7a8165d
Source dataset
uspto-grants-2007_01
Patent number
US07160909B2

Reaction notes

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