Lithium hydroxide, monohydrate → 4-[2-(1-{2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl}-piperidine-4-carbonyl)-benzoimidazol-1-yl]-butyric acid

HRID 2269861Notes

Reaction equation

HRID 2269861 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:48]=[C:49]([O:53][CH3:54])[C:50]=1[O:51][CH3:52])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([C:29]([C:31]3[N:35]([CH2:36][CH2:37][CH2:38][C:39]([O:41]CC)=[O:40])[C:34]4[CH:44]=[CH:45][CH:46]=[CH:47][C:33]=4[N:32]=3)=[O:30])[CH2:25][CH2:24]2)([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:9]1)=[O:7].O.[OH-].[Li+].O1CCCC1.O>O>[CH3:54][O:53][C:49]1[CH:48]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:50]=1[O:51][CH3:52])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([C:29]([C:31]3[N:35]([CH2:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40])[C:34]4[CH:44]=[CH:45][CH:46]=[CH:47][C:33]=4[N:32]=3)=[O:30])[CH2:25][CH2:24]2)([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 101472184-[2-(1-{2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl}-piperidine-4-carbonyl)-benzoimidazol-1-yl]-butyric acid ethyl esterHCID 21881883Oxolane--water (1/1)

Product 1

HCID 103058884-[2-(1-{2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl}-piperidine-4-carbonyl)-benzoimidazol-1-yl]-butyric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1-(3-ethoxycarbonyl-propyl)-1 H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-(3,4-dichloro-phenyl)-pyrrolidine (0.32 g, 0.41 mmol) and lithium hydroxide hydrate (0.052 g, 1.23 mmol) in 4/1 tetrahydrofuran/water (20 mL). After 20 hours, dilute the reaction mixture with water and evaporate in vacuo to remove most of the tetrahydrofuran. Acidify to pH 2 using 1 M hydrochloric acid solution and cool to 5° C. to obtain a solid. Collect the solid by filtration. Suspend the solid in diethyl ether (150 mL) and stir. After 18 hours, collect the solid by filtration and dry to give the title compound: mp; 125-140° C. Elemental Analysis calculated for C39H44Cl2N4O7·HCl: C 59.43; H 5.75; N 7.11; Found: C 59.55; H 5.81; N 6.94.

Workup

  1. customevaporate in vacuo
  2. customto remove most of the tetrahydrofuran
  3. customto obtain a solid
  4. customCollect the solid
  5. filtrationby filtration
  6. waitAfter 18 hours
  7. customcollect the solid
  8. filtrationby filtration
  9. customdry

Sources & evidence

ORD record
ord-7ef37a75824240c1ab1a47cd965dd0d9
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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