Lithium hydroxide, monohydrate → 4-[2-(1-{2-[3-Phenyl-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl}-piperidine-4-carbonyl)-benzoimidazol-1-ylmethyl]-benzoic acid; hydrochloride

HRID 2269864Notes

Reaction equation

HRID 2269864 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:49]=[C:50]([O:54][CH3:55])[C:51]=1[O:52][CH3:53])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([C:27]([C:29]3[N:33]([CH2:34][C:35]4[CH:40]=[CH:39][C:38]([C:41]([O:43]C)=[O:42])=[CH:37][CH:36]=4)[C:32]4[CH:45]=[CH:46][CH:47]=[CH:48][C:31]=4[N:30]=3)=[O:28])[CH2:23][CH2:22]2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)=[O:7].O.[OH-].[Li+].O1CCCC1.O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:49]=[C:50]([O:54][CH3:55])[C:51]=1[O:52][CH3:53])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH:24]([C:27]([C:29]3[N:33]([CH2:34][C:35]4[CH:36]=[CH:37][C:38]([C:41]([OH:43])=[O:42])=[CH:39][CH:40]=4)[C:32]4[CH:45]=[CH:46][CH:47]=[CH:48][C:31]=4[N:30]=3)=[O:28])[CH2:25][CH2:26]2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 10234086HCID 10234086, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 101230404-[2-(1-{2-[3-Phenyl-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl}-piperidine-4-carbonyl)-benzoimidazol-1-ylmethyl]-benzoic acid; hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1-(4-methoxycarbonyl-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-phenyl-pyrrolidine (0.68 g, 0.92 mmol) and lithium hydroxide hydrate (0.12 g, 2.75 mmol) in 4/1 tetrahydrofuran/water (45 mL). After 72 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 to obtain a solid. Collect the solid by filtration. Suspend the solid in diethyl ether (150 mL) and stir. Collect the solid by filtration and dry to give the title compound: mp; 173.0-190.0° C.

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. customCollect the solid
  7. filtrationby filtration
  8. customdry

Sources & evidence

ORD record
ord-934e208631e04e228f0f52ca0b686b14
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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