Lithium Hydroxide → HCID 11281695, compound

HRID 489107Notes

Reaction equation

HRID 489107 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:14]=[C:13]2[CH2:15][CH2:16][CH2:17][C:12]2=[C:11]2[C:7]=1[C:8]([C:27](=[O:31])[C:28]([NH2:30])=[O:29])=[C:9]([CH3:26])[N:10]2[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1.[OH-].[Li+]>O1CCCC1.CO>[NH2:30][C:28](=[O:29])[C:27]([C:8]1[C:7]2[C:11](=[C:12]3[CH2:17][CH2:16][CH2:15][C:13]3=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:32])=[O:2])[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:9]=1[CH3:26])=[O:31]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10138016HCID 10138016, compound

Product 1

HCID 11281695HCID 11281695, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(4-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (0.34 g, 0.78 mmol) in tetrahydrofuran (15 mL) and methanol (15 mL) was treated with 1 M aqueous lithium hydroxide solution (20 mL) at room temperature for 66 h. The mixture was concentrated in vacuo and the residue acidified with concentrated hydrochloric acid. The resulting precipitate was collected via vacuum filtration, washed with water, and air-dried to provide 168 mg (51%) of the title compound as a green solid: mp 199-201° C. (dec). 1H NMR (DMSO-d6) δ 13.10 (bs, 1H), 7.18 (m, 2H), 6.95 (m, 2H), 6.50 (s, 1H), 5.55 (s, 2H), 4.62 (s, 2H), 2.95 (t, J=6.6 Hz, 2H), 2.83 (t, J=7.0 Hz, 2H), 2.50 (s, 3H), 1.98 (quintet, J=7.3 Hz, 2H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationThe resulting precipitate was collected via vacuum filtration
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-6e24d82d0afb4ceb98cad4b25e9ddd61
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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