Lithium Hydroxide → HCID 69744939, compound

HRID 489105Notes

Reaction equation

HRID 489105 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]=[C:21]([F:25])[CH:20]=1.[OH-].[Li+]>O1CCCC1.CO>[OH2:2].[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]=[C:21]([F:25])[CH:20]=2)[C:9]=1[CH3:26])=[O:31]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10181617HCID 10181617, compound

Product 1

HCID 69744939HCID 69744939, compoundYield 154.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(3-fluorobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (500 mg, 1.14 mmol) in tetrahydrofuran (20 mL) and methanol (20 mL) was treated with 1 M aqueous lithium hydroxide (25 mL) at room temperature for 18 h. The resulting suspension was concentrated in vacuo and the residue diluted with water and adjusted to pH 2 with concentrated hydrochloric acid. After stirring for 1 h, the resulting precipitate was collected via vacuum filtration to provide 390 mg (77%) of the title compound as a solid. Recrystallization (methanol/water) of the residue provided an analytical sample as a yellow-green fibrous solid: mp 250-252° C. 1H NMR (DMSO-d6) δ 12.87 (bs, 1H), 7.71 (s, 1H), 7.42 (s, 1H), 7.37 (m, 1H), 7.10 (dt, J=10.6, 2.2 Hz, 1H), 6.77 (d, J=9.9 Hz, 1H), 6.69 (d, J=7.7 Hz, 1H), 6.47 (s, 1H), 5.56 (s, 2H), 4.62 (s, 2H), 2.93 (t, J=7.0 Hz, 2H), 2.82 (t, J=7.0 Hz, 2H), 2.41 (s, 3H), 1.97 (quintet, J=7.3 Hz, 2H); MS ES− m/e 423 (p−1); IR (KBr, cm−1) 3438, 1617, 1376.

Workup

  1. concentrationThe resulting suspension was concentrated in vacuo
  2. additionthe residue diluted with water
  3. filtrationthe resulting precipitate was collected via vacuum filtration

Sources & evidence

ORD record
ord-8fd04765cac84cf39aa56676a63ed2cb
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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