Diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-[1-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylmethyl)-1H-imidazol-4-yl]malonate → 6-Amino-2-[1-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylmethyl)-1H-imidazol-4-yl]-hexanoic acid
Reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:24]1[N:25]=[CH:26][N:27]([CH2:29][C:30]2[S:31][C:32]([CH:35]3[CH2:37][CH2:36]3)=[N:33][N:34]=2)[CH:28]=1)(C(OCC)=O)[C:14]([O:16]CC)=[O:15])=O)(C)(C)C>Cl>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:24]1[N:25]=[CH:26][N:27]([CH2:29][C:30]2[S:31][C:32]([CH:35]3[CH2:37][CH2:36]3)=[N:33][N:34]=2)[CH:28]=1)[C:14]([OH:16])=[O:15]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
0.140 g (261 μmol) of diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-[1-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylmethyl)-1H-imidazol-4-yl]malonate was suspended in 10 ml of semi-concentrated hydrochloric acid, and the mixture was heated with stirring at 95° C. for 8 h. The reaction mixture was concentrated under reduced pressure and purified by preparative HPLC, and the product-containing fractions were freeze-dried and then taken up in 2.5 eq of 1N hydrochloric acid and freeze-dried and taken up in water and freeze-dried. The preparation was then purified once more by preparative HPLC, and the product-containing fractions were freeze-dried. This gave 35 mg (32%) of the title compound as trifluoroacetic acid salt.
Workup
- temperaturethe mixture was heated
- concentrationThe reaction mixture was concentrated under reduced pressure
- custompurified by preparative HPLC
- customthe product-containing fractions were freeze-dried
- customfreeze-dried
- customfreeze-dried
- customThe preparation was then purified once more by preparative HPLC
- customthe product-containing fractions were freeze-dried
Sources & evidence
- ORD record
- ord-5cc0dbdec2de4e8688402674d79d74c3
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08044208B2
Reaction notes
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