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Methanol → Ethyl 2-(3-aminoazetidin-1-yl)-1,3-benzothiazole-7-carboxylate

HRID 1425363
Notes
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Reaction equation

HRID 1425363 reaction equation
Cl.C(OCC)(=O)C.CO.C(OC([NH:17][CH:18]1[CH2:21][N:20]([C:22]2[S:23][C:24]3[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)[CH2:19]1)=O)(C)(C)C.C1COCC1>O1CCOCC1>[NH2:17][CH:18]1[CH2:21][N:20]([C:22]2[S:23][C:24]3[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)[CH2:19]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 21866389Hydrogen chloride-ethyl acetateHCID 67548709Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-1,3-benzothiazole-7-carboxylate

Product 1

HCID 67549305Ethyl 2-(3-aminoazetidin-1-yl)-1,3-benzothiazole-7-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 4 N hydrochloric acid/ethyl acetate solution (2.66 mL, 10.7 mmol) and methanol (5 mL) were added to a solution of ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-1,3-benzothiazole-7-carboxylate obtained in Example (224a) (402 mg, 1.07 mmol) in 1,4-dioxane (11 mL) at room temperature, followed by stirring for 17 hours. Then, THF (5 mL) was added, and the mixture was further stirred for 31 hours. The reaction solution was concentrated, and saturated aqueous sodium bicarbonate solution was added to the resulting residue. Thereafter, the mixture was extracted with ethyl acetate, and the combined organic layers were dried over anhydrous magnesium sulfate. Following filtration, the solvent was evaporated under reduced pressure to obtain 281 mg of the title compound as a pale yellow solid (95%).

Workup

  1. stirringthe mixture was further stirred for 31 hours
  2. concentrationThe reaction solution was concentrated
  3. additionsaturated aqueous sodium bicarbonate solution was added to the resulting residue
  4. extractionThereafter, the mixture was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltration
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aae51b9997fe4daf9d06c6bae8b4efaa
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927588B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes