1,4-Dioxane hydrochloride → Ethyl 2-[(3S,4R)-3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl]-1,3-benzothiazole-7-carboxylate

HRID 43850Notes

Reaction equation

HRID 43850 reaction equation
Cl.O1CCOCC1.C(OC([NH:15][C@@H:16]1[C@H:21]([NH:22][C:23]([C:25]2[NH:26][C:27]([CH2:31][CH3:32])=[C:28]([Cl:30])[N:29]=2)=[O:24])[CH2:20][CH2:19][N:18]([C:33]2[S:34][C:35]3[C:41]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:40][CH:39]=[CH:38][C:36]=3[N:37]=2)[CH2:17]1)=O)(C)(C)C>>[NH2:15][C@@H:16]1[C@H:21]([NH:22][C:23]([C:25]2[NH:26][C:27]([CH2:31][CH3:32])=[C:28]([Cl:30])[N:29]=2)=[O:24])[CH2:20][CH2:19][N:18]([C:33]2[S:34][C:35]3[C:41]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:40][CH:39]=[CH:38][C:36]=3[N:37]=2)[CH2:17]1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67549168HCID 67549168, compound

Product 1

HCID 67548804Ethyl 2-[(3S,4R)-3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl]-1,3-benzothiazole-7-carboxylateYield 100%

Procedure

A 4 N hydrochloric acid/1,4-dioxane solution (3 mL) was added to ethyl 2-[(3S,4R)-3-[(tert-butoxycarbonyl)amino]-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl]-1,3-benzothiazole-7-carboxylate obtained in Example (202d) (121 mg, 0.210 mmol), and the mixture was stirred at room temperature for one hour. The reaction solution was concentrated under reduced pressure. Saturated aqueous sodium bicarbonate solution was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 v/v) to obtain 100 mg of the title compound (100%) as a colorless solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionSaturated aqueous sodium bicarbonate solution was added to the resulting residue
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe filtrate was concentrated
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 v/v)

Sources & evidence

ORD record
ord-2f540378addf435fa32ea86dcd9432b9
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

Loading…