Lithium Hydroxide → HCID 10223013, compound

HRID 489103Notes

Reaction equation

HRID 489103 reaction equation
C[O:2][C:3](=[O:31])[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:26](=[O:30])[C:27]([NH2:29])=[O:28])=[C:9]([CH3:25])[N:10]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Li+]>CO.O1CCCC1>[NH2:29][C:27](=[O:28])[C:26]([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:31])=[O:2])[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]=1[CH3:25])=[O:30]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10223886HCID 10223886, compound

Product 1

HCID 10223013HCID 10223013, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-benzyl-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (95 mg, 0.23 mmol) in a 1:1 mixture of methanol/tetrahydrofuran (1 mL) was treated with excess 1M lithium hydroxide for 19 h at room temperature. The mixture was concentrated in vacuo, diluted with water, and acidified with 5N hydrochloric acid. The resulting precipitate was collected via vacuum filtration and recrystallized (absolute ethanol) to provide 65 mg (71%) of the title product as yellow crystals: mp 255-257° C. 1H NMR (DMSO6) δ 12.84 (bs, 1H, —OH), 7.69 (bs, 1H), 7.33 (m, 4H), 6.92 (d, J=7.0 Hz, 2H), 6.46 (s, 1H), 5.54 (s, 2H), 4.61 (s, 2H), 2.95 (t, J=7.0 Hz, 2H), 2.82 (t, J=7.3 Hz, 2H), 2.42 (s, 3H), 1.96 (quintet, J=7.0 Hz, 2H); MS ES+ m/e 407 (p+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with water
  3. filtrationThe resulting precipitate was collected via vacuum filtration
  4. customrecrystallized (absolute ethanol)

Sources & evidence

ORD record
ord-41f314d526ab49ee8840e1a006717f1e
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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