Home Cart Sign in  
Chemical Structure| 142253-55-2 Chemical Structure| 142253-55-2
Chemical Structure| 142253-55-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

1-N-Boc-3-Azetidinecarboxylic acid is a protected azetidine-3-carboxylic acid derivative with the amino group protected by tert-butoxycarbonyl (Boc), used for the synthesis of antibody-drug conjugates (ADCs) and protein degraders (PROTACs).

Synonyms: 1-Boc-azetidine-3-carboxylic acid

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of 1-N-Boc-3-Azetidinecarboxylic acid

CAS No. :142253-55-2
Formula : C9H15NO4
M.W : 201.22
SMILES Code : O=C(C1CN(C(OC(C)(C)C)=O)C1)O
Synonyms :
1-Boc-azetidine-3-carboxylic acid
MDL No. :MFCD01860897
InChI Key :NCADHSLPNSTDMJ-UHFFFAOYSA-N
Pubchem ID :2755981

Safety of 1-N-Boc-3-Azetidinecarboxylic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 1-N-Boc-3-Azetidinecarboxylic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 142253-55-2 ]
  • Downstream synthetic route of [ 142253-55-2 ]

[ 142253-55-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 142253-55-2 ]
  • [ 486415-29-6 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With triethylamine; isobutyl chloroformate In tetrahydrofuran at -20 - -10℃; for 0.25 h;
Stage #2: With ammonium hydroxide In tetrahydrofuran at -20 - 20℃; for 1 h;
1-[(tert-butoxy)carbonyl]azetidine-3-carboxylic acid (4.96 g, 24.65 mmol) and TEA (5.84 ml, 42.0 mmol) were dissolved in THF (60 ml) and cooled to -20°C. Isobutyl chloroformate (4.8 ml, 37.0 mmol) was added slowly and the reaction mixture stirred at ^10°C for 15 min. 28percent aqueous ammonia (7.46 ml, 394 mmol) was added and the mixture allowed to warm to room temperature and stirred for 1 h. The reaction mixture was quenched with sat. NaHC<(aq) and extracted with DCM (3 x 100 ml). The combined organic extracts were dried (Na2S04), filtered and evaporated in vacuo. Purification by flash chromatography using a gradient elution of 20-100percent EtOAc / heptane followed by 1-4percent MeOH / EtOAc afforded the title compound (3.99 g, 81 percent) as a white solid. 1 H-NMR (CDCI3, 250 MHz): d[ppm]= 5.47 (s, 2H), 4.22 - 4.01 (m, 4H), 3.34 - 3.15 (m, 1 H), 1 .46 (s, 9H) HPLCMS (Method A): [m/z]: 222.95 [M+Na]+
63% With ammonium acetate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; To a solution of 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (from Activate Scientific. 0.25 g, 1.2 mmol), ammonium acetate (0.14 g, 1.9 mmol) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.71 g, 1.9 mmol) in N,N-dimethylformamide (4 mL) was added N,N-diisopropylethylamine (0.43 mL, 2.5 mmol). The mixture was stirred at room temperature overnight. The mixture was diluted with MeOH and purified on prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1percent ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (0.156 g, 63percent). LCMS calculated for C9H16N2O3Na (M+Na)+: m/z=223.1. Found: 223.0
References: [1] Patent: WO2017/68089, 2017, A2, . Location in patent: Page/Page column 234; 235.
[2] Patent: US2014/121198, 2014, A1, . Location in patent: Paragraph 0688; 0689.
[3] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 5, p. 757 - 761.
[4] Patent: WO2010/60952, 2010, A1, . Location in patent: Page/Page column 81.
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3037 - 3040.
  • 2
  • [ 142253-55-2 ]
  • [ 870089-49-9 ]
References: [1] Patent: WO2014/173289, 2014, A1, .
[2] Patent: TWI602818, 2017, B, .
[3] Patent: WO2018/137573, 2018, A1, .
[4] Patent: US2015/361067, 2015, A1, .
[5] Patent: US2008/58348, 2008, A1, .
[6] Patent: WO2011/61214, 2011, A1, .
 

Historical Records

Technical Information

Categories