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Diethyl Ether → HCID 22009300, compound

HRID 323289
Notes
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Reaction equation

HRID 323289 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]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([NH:27][C:28]3[N:32]([CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[C:40]([O:42]C)=[O:41])[C:31]4[CH:44]=[CH:45][CH:46]=[CH:47][C:30]=4[N:29]=3)[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+].[CH3:58][S:59]([OH:62])(=[O:61])=[O:60].C(OCC)C>O1CCCC1.O>[CH3:58][S:59]([OH:62])(=[O:61])=[O:60].[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]([CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH:24]([NH:27][C:28]3[N:32]([CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[C:40]([OH:42])=[O:41])[C:31]4[CH:44]=[CH:45][CH:46]=[CH:47][C:30]=4[N:29]=3)[CH2:25][CH2:26]2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 168937Lithium hydroxide, monohydrateHCID 9896732HCID 9896732, compound

Product 1

HCID 22009300HCID 22009300, compound

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-methoxycarbonylbenzyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-phenylpyrrolidine (0.6 g, 0.8 mmol) and lithium hydroxide hydrate (0.11 g, 2.4 mmol) in tetrahydrofuran (24 mL) and water (8 mL). After 18 hours, evaporate the reaction mixture in vacuo to remove the tetrahydrofuran to obtain a solid. Collect the solid and add tetrahydrofuran (40 mL). Add a solution of methanesulfonic acid (0.24 g, 2.6 mmol) in tetrahydrofuran (3 mL). Add diethyl ether (200 mL) to give a residue. Decant the supernatant, add diethyl ether, and stir to give a solid. Collect the solid and dry in vacuo to give the title compound: mp; 161-175° C.

Workup

  1. customevaporate the reaction mixture in vacuo
  2. customto remove the tetrahydrofuran
  3. customto obtain a solid
  4. customCollect the solid
  5. additionadd tetrahydrofuran (40 mL)
  6. customDecant the supernatant
  7. additionadd diethyl ether
  8. customto give a solid
  9. customCollect the solid
  10. customdry in vacuo

Sources & evidence

ORD record
ord-cb92093ff0a64665953fd39aa6a36627
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211199B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes