Lithium Hydroxide → HCID 10224177, compound

HRID 489106Notes

Reaction equation

HRID 489106 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][CH:22]=[CH:21][C:20]=1[F:25].[OH-].[Li+]>O1CCCC1.CO.O>[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][CH:22]=[CH:21][C:20]=2[F:25])[C:9]=1[CH3:26])=[O:31]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 11166515HCID 11166515, compound

Product 1

HCID 10224177HCID 10224177, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(2-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (345 mg, 0.787 mmol) in tetrahydrofuran (20 mL) and methanol (20 mL) was treated with 1 M aqueous lithium hydroxide solution (25 mL) at room temperature for 19 h. The mixture was diluted with water and methanol and filtered. The filtrate was concentrated in vacuo and the residue dissolved in water and acidified with concentrated hydrochloric acid. The resulting precipitate was collected via vacuum filtration, washed with water, and air-dried to provide 165 mg (50%) of the title compound as a yellow solid. Recrystallization (methanol/water) provided an analytical sample as a yellow green solid: mp 246-249° C. (dec). 1H NMR (DMSO-d6) δ 12.94 (bs, 1H), 7.73 (bs, 1H), 7.44 (bs, 1H), 7.33 (m, 2H), 7.11 (t, J=7.6 Hz, 1H), 6.48 (s, 1H), 6.37 (t, J=7.6 Hz, 1H), 5.59 (s, 2H), 4.63 (s, 2H), 2.92 (t, J=7.3.Hz, 2H), 2.83 (t, J=7.3 Hz, 2H), 2.44 (s, 3H), 1.97 (quintet, J=7.3 Hz, 2H); MS ES+ m/e 425 (p+1); IR (KBr, cm−1) 3450, 1619, 1225.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionthe residue dissolved in water
  4. filtrationThe resulting precipitate was collected via vacuum filtration
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-9381b297c0b94ace8ab306de56d0490f
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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