ChemicalBook > CAS DataBase List > (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID

(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID

Product Name
(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID
CAS No.
197142-36-2
Chemical Name
(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID
Synonyms
Azabicyclo BOC acid impurity;N-Boc-L-cis-4,5-methanoproline;-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;(1s,3s,5s)-2-boc-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;(1S,3S,5S)-N2-BOC-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID;(1S,3S,5S)-2-Boc-2-aza-bicyclo[3.1.0]hexane-3-dicarboxylic acid;(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID;(3S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid;2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) ester, (1S,3S,5S)-;(1S,3S,5S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
CBNumber
CB2825254
Molecular Formula
C11H17NO4
Formula Weight
227.26
MOL File
Mol file
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(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID Property

Boiling point:
355.9±25.0 °C(Predicted)
Density 
1.276±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
pka
4.03±0.20(Predicted)
Appearance
Light yellow to yellow Solid
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
B692925
Product name
(1S,3S,5S)-2-Boc-2-azabicyclo[3.1.0]hexane-3-carboxylicAcid
Packaging
10mg
Price
$155
Updated
2021/12/16
Activate Scientific
Product number
AS59843
Product name
(1S,3S,5S)-2-Boc-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
Purity
97% ee
Packaging
1g
Price
$555
Updated
2021/12/16
AK Scientific
Product number
9735BB
Product name
(1S,3S,5S)-2-(Tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylicacid
Packaging
1g
Price
$879
Updated
2021/12/16
Matrix Scientific
Product number
133494
Product name
(1S,3S,5S)-2-(tert-Butoxycarbonyl)-2-azabicyclo-[3.1.0]hexane-3-carboxylicacid
Purity
97%
Packaging
1g
Price
$990
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CCH0003936
Product name
(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID
Purity
95.00%
Packaging
1G
Price
$1355.55
Updated
2021/12/16
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(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID Chemical Properties,Usage,Production

Uses

(1S,3S,5S)-2-Boc-2-azabicyclo[3.1.0]hexane-3-carboxylic Acid is an impurity of Saxagliptin (S143500), which is a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration and has a pharmacokinetic profile compatible with once daily dosing.

Synthesis

214193-11-0

197142-36-2

The general procedure for the synthesis of (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid using (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid ester as raw material is as follows: the (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo [3.1.0]hexane-3-carboxylic acid (1.4 g) was dissolved in a mixed solvent of methanol (40 mL) and tetrahydrofuran (20 mL), 1N lithium hydroxide solution (10 mL) was added and the reaction was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was acidified to pH 4.5 with 2N hydrochloric acid and stirring was continued for 15 min at room temperature. Subsequently, the reaction mixture was extracted with ethyl acetate, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford the target product (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (1.2 g, 96% yield, MNa+ = 250).

References

[1] Patent: WO2006/116157, 2006, A2. Location in patent: Page/Page column 114-115
[2] Patent: EP2272825, 2015, B1. Location in patent: Paragraph 0180; 0181
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 45, p. 13268 - 13272
[4] Angew. Chem., 2015, # 45, p. 13466 - 13470,4
[5] Patent: CN106928124, 2017, A. Location in patent: Paragraph 0037; 0083-0088

(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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(1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID Suppliers

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197142-36-2, (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACIDRelated Search:

Saxagliptin Impurity 15 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3R,5S)- 1H-Cyclopropa[4,5]pyrrolo[1,2-a]pyrazine-3,6-dione, hexahydro-4-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-, (1aS,4S,6aR,7aS)- Saxagliptin Impurity 16 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3R,5R)- (1R,3S,5R)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXAMIDE 2,2,2-TRIFLUOROACETIC ACID 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3S,5S)- (1R,3R,5R)-2-Azabicyclo[3.1.0]hexane-3-carboxamide 2,2,2-trifluoroacetate Tricyclo[3.3.1.13,7]decane-1-acetic acid, α-[[(1,1-diMethylethoxy)carbonyl]aMino]-3,5-dihydroxy-, (αS)- (S) - N- Boc- adamantylglycine 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3S,5R)- 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3R,5R)- 3H-Cyclopropa[4,5]pyrrolo[1,2-a]pyrazin-3-one, 6-aMino-1,1a,4,6a,7,7a-hexahydro-4-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-, (1aS,4S,6aR,7aS)- 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3R,5S)- Saxagliptin Impurity 34 Saxagliptin iMpurity (R)-N-Boc-3-hydroxyadaMantylglycine axagliptin Impurity 28 Mesylate

  • (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID
  • (1s,3s,5s)-2-boc-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
  • (1S,3S,5S)-N2-BOC-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID
  • N-Boc-L-cis-4,5-methanoproline
  • -2-azabicyclo[3.1.0]hexane-3-carboxylic acid
  • (1S,3S,5S)-2-Boc-2-aza-bicyclo[3.1.0]hexane-3-dicarboxylic acid
  • (3S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
  • (1S,3S,5S)-2-[(2-methylpropan-2-yl)oxycarbonyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid
  • 2-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid, 2-(1,1-dimethylethyl) ester, (1S,3S,5S)-
  • Azabicyclo BOC acid impurity
  • 197142-36-2