| Identification | More | [Name]
1-N-Boc-3-Azetidinecarboxylic acid | [CAS]
142253-55-2 | [Synonyms]
1-BOC-AZETIDINE-3-CARBOXYLIC ACID
1-N-BOC-3-AZETIDINECARBOXYLIC ACID
1-(TERT-BUTOXYCARBONYL)AZETIDINE-3-CARBOXYLIC ACID
AZETIDINE-1,3-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER
AZETIDINE-3-CARBOXYLIC ACID, N-BOC PROTECTED
BOC-AZE(3)-OH
BOC-AZETIDINE-3-CARBOXYLIC ACID
N-ALPHA-T-BOC-L-AZETIDINE-3-CARBOXYLIC ACID
N-ALPHA-T-BUTOXYCARBONYL-AZETIDE-3-CARBOXYLIC ACID
N-ALPHA-T-BUTOXYCARBONYL-AZETIDINE-3-CARBOXYLIC ACID
N-BOC-3-AZETIDINE CARBOXYLIC ACID
N-BOC-AZETIDINE-3-CARBOXYLIC ACID
RARECHEM BK PT 0278
BOC-AZETIDINE-3-CARBOXYLIC ACID 98%
1-Boc-Azetidine3-Carboxylicacide
Azetidine-3-carboxylic acid, N-BOC protected 97%
1-N-Boc-Azetidine-3-carboxylic acid
3-carboxyazetidine-1-carboxylic acid tert-butyl ester
1-BOC-AZETIDINE-3-CARBOXYLIC ACID 98+% | [Molecular Formula]
C9H15NO4 | [MDL Number]
MFCD01860897 | [Molecular Weight]
201.22 | [MOL File]
142253-55-2.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow powder | [Melting point ]
100.1-101.9°C | [Boiling point ]
321.0±35.0 °C(Predicted) | [density ]
1.246±0.06 g/cm3(Predicted) | [storage temp. ]
Store at-15°C | [form ]
Crystalline Powder | [pka]
4.21±0.20(Predicted) | [color ]
White | [BRN ]
8832105 | [InChI]
InChI=1S/C9H15NO4/c1-9(2,3)14-8(13)10-4-6(5-10)7(11)12/h6H,4-5H2,1-3H3,(H,11,12) | [InChIKey]
NCADHSLPNSTDMJ-UHFFFAOYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CC(C(O)=O)C1 | [CAS DataBase Reference]
142253-55-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37:Wear suitable gloves .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
No | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow powder | [Uses]
peptide synthesis | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
General procedure for the synthesis of 1-Boc-azetidine-3-carboxylic acid from di-tert-butyl dicarbonate and 3-acridinecarboxylic acid:
Example 4 Synthesis of 6-(3-{[(benzylsulfonyl)amino]carbonyl}azetidin-1-yl)-5-cyano-2-(difluoromethyl)nicotinate
(a) Preparation of ethyl 1-(tert-butoxycarbonyl)azetidine-3-carboxylate
Di-tert-butyl dicarbonate (25.535 g, 117 mmol) dissolved in methanol (70 mL) was added dropwise to a stirred solution of azetidine-3-carboxylic acid (10.11 g, 100 mmol) and triethylamine (27.8 mL, 200 mmol) in methanol (105 mL) over a period of 20 min. The reaction was carried out at room temperature (mild exotherm was observed) with continuous stirring for 18 hours. Upon completion of the reaction, the mixture was evaporated to dryness, tetrahydrofuran (120 mL) was added and evaporated again to afford the crude 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid, which could be used in the next step without further purification.
Yield: 25.89 g (128%).
1H NMR (400 MHz, CDCl3) δ 1.43 (9H, s), 3.21-3.34 (1H, m), 4.00-4.13 (4H, m). | [References]
[1] Patent: WO2008/4946, 2008, A1. Location in patent: Page/Page column 90-91
[2] Patent: US2008/171732, 2008, A1. Location in patent: Page/Page column 36
[3] Patent: WO2008/85119, 2008, A1. Location in patent: Page/Page column 175-176
[4] Patent: WO2008/108957, 2008, A2. Location in patent: Page/Page column 98
[5] Patent: WO2008/95912, 2008, A2. Location in patent: Page/Page column 77 |
|
|