| Identification | Back Directory | [Name]
(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester | [CAS]
361440-67-7 | [Synonyms]
SGB
EOS-60426
Saxagliptin int
Saxagliptin INT 2
N-Boc-cis-4,5-Methano-L-prolinamide
N-Boc-L-cis-4,5-MethanoprolineaMide
SAXAGLIPTIN CAS 3611442-04-8 INTERMEDIATES
(1S,3S,5S)-2-Boc-2-azabicyclo-[3.1.0]hexane-3-carboxamide
-tert-Butyl 3-carbamoyl-2-azabicyclo[3.1.0]hexane-2-carboxylate
(1S,3S,5S)-2-(tert-butyl)-2-azabicyclo[3.1.0]hexane-3-carboxamide
tert-butyl(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hexane-2-carboxylate
(1S,3S,5S)-3-(AMinocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid
(1S,3S,5S)-tert-butyl 3-carbaMoyl-2-azabicyclo[3.1.0]hexane-2-carboxylate
ABHB (1S,3S,5S)-tert-butyl 3-carbamoyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylate
(1S, 3S, 5S) -3- (amino-carbonyl) -2-azabicyclic [3.1.0] hexane-2-tert-butyl carboxylate
(1S,3S,5S)-3-(AMinocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl este
(1S,3S,5S)-3-(AMinocarbonyl)-2-azabicylo[3.1.0]hexane-2-carboxylic acid tert-butyl ester
(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester
(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acidd tert-butyl ester
(1S,3S,5S)-3-(AMINOCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER1S
(1S,3S,5S)-3-Aminocarbonyl-2-Azabicyclo[3.1.0]Hexane-2-Carboxylicacid,1,1-Dimethylethyl Ester
2-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 3-(aminocarbonyl)-, 1,1-dimethylethyl ester, (1S,3S,5S)-
(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester(For export only)
(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester ISO 9001：2015 REACH | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C11H18N2O3 | [MDL Number]
MFCD13151933 | [MOL File]
361440-67-7.mol | [Molecular Weight]
226.27 |
| Chemical Properties | Back Directory | [Boiling point ]
388.9±21.0 °C(Predicted) | [density ]
1.228 | [storage temp. ]
Sealed in dry,2-8°C | [pka]
16.00±0.20(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C11H18N2O3/c1-11(2,3)16-10(15)13-7-4-6(7)5-8(13)9(12)14/h6-8H,4-5H2,1-3H3,(H2,12,14)/t6-,7-,8-/m0/s1 | [InChIKey]
VLAGXRRGXCNITB-FXQIFTODSA-N | [SMILES]
[C@@]12([H])[C@@]([H])(C1)C[C@@H](C(N)=O)N2C(OC(C)(C)C)=O |
| Hazard Information | Back Directory | [Uses]
N-Boc-L-cis-4,5-Methanoprolineamide is an intermediate used to prepare methanoprolinenitrile-contg. dipeptide mimetics as DPP-IV inhibitors and as antidiabetic agents. | [Synthesis]
At -15°C, (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (1.2 g) was dissolved in THF (20 ml) and 4-methylmorpholine (710 μl) was added. Subsequently, isobutyl chloroformate (780 μl) was added slowly over a period of 5 min and stirring was continued at this temperature for 30 min. The reaction system was cooled to -30°C and aqueous ammonia solution (25 ml, 0.5 M) dissolved in dioxane was slowly added. The reaction mixture was stirred at -30 °C for 30 min and then gradually warmed to room temperature and continued stirring overnight. After completion of the reaction, the pH was adjusted to 4.5 with 10% aqueous citric acid solution and extracted with ether (3 x 50 ml). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Finally, purification by silica gel column chromatography (eluent: cyclohexane/ethyl acetate, 1:10) afforded the target product (1S,3S,5S)-tert-butyl (1.0 g, 84% yield, MNa+ = 248) of (1S,3S,5S)-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate. | [References]
[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 10, p. 2587 - 2598
[2] Patent: WO2006/116157, 2006, A2. Location in patent: Page/Page column 114-116
[3] Patent: EP2272825, 2015, B1. Location in patent: Paragraph 0182; 0183
[4] Patent: CN106928124, 2017, A. Location in patent: Paragraph 0037; 0095-0100 |
|
|