Hydrogen chloride-ethyl acetate → HCID 86648865, compound

HRID 43985Notes

Reaction equation

HRID 43985 reaction equation
[ClH:1].C(OCC)(=O)C.[Cl:8][C:9]1[N:10]=[C:11]([C:16]([NH:18][C@H:19]2[CH2:24][CH2:23][N:22]([C:25]3[S:26][C:27]([C:31]([NH:33][CH:34]4[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35]4)=[O:32])=[C:28]([CH3:30])[N:29]=3)[CH2:21][C@H:20]2[O:47][CH3:48])=[O:17])[NH:12][C:13]=1[CH2:14][CH3:15]>CO>[ClH:8].[ClH:1].[Cl:8][C:9]1[N:10]=[C:11]([C:16]([NH:18][C@H:19]2[CH2:24][CH2:23][N:22]([C:25]3[S:26][C:27]([C:31]([NH:33][CH:34]4[CH2:35][CH2:36][NH:37][CH2:38][CH2:39]4)=[O:32])=[C:28]([CH3:30])[N:29]=3)[CH2:21][C@H:20]2[O:47][CH3:48])=[O:17])[NH:12][C:13]=1[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86648864tert-Butyl cis(+/-)-4-({[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazol-5-yl]carbonyl}amino)piperidine-1-carboxylate

Product 1

HCID 86648865HCID 86648865, compoundYield 144.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4 N hydrochloric acid/ethyl acetate solution (2 ml, 8 mmol) was added to a solution of tert-butyl cis(±)-4-({[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-thiazol-5-yl]carbonyl}amino)piperidine-1-carboxylate obtained in Example (266a) (30 mg, 0.05 mmol) in methanol (0.4 mL), followed by stirring for 30 minutes. The solvent was evaporated under reduced pressure. The residue was solidified by adding ethyl acetate, diethyl ether and hexane, to obtain 21 mg of the title compound as a cream-colored solid (72%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionby adding ethyl acetate, diethyl ether and hexane

Sources & evidence

ORD record
ord-f7eec6c22567444a84d306e288d81bc5
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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