BOC-L-PYROGLUTAMIC ACID BENZYL ESTER
- Product Name
- BOC-L-PYROGLUTAMIC ACID BENZYL ESTER
- CAS No.
- 113400-36-5
- Chemical Name
- BOC-L-PYROGLUTAMIC ACID BENZYL ESTER
- Synonyms
- (S)-2-Benzyl 1-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate;N-BOC-L-Pyroglutamic acid benzyl ester;PYR294;Boc-Pyr-Obzl;Boc-Pyr-Obzl-OH;(Tert-Butoxy)Carbonyl Pyr-OBzl;Boc-l-pyroglutamate benzyl ester;Boc-PyroglutaMic acid. Benzyl ester;BOC-L-PYROGLUTAMIC ACID BENZYL ESTER;BOC-L-PYROGLUTAMIC ACID BENZYL ESTER USP/EP/BP
- CBNumber
- CB11505325
- Molecular Formula
- C17H21NO5
- Formula Weight
- 319.35
- MOL File
- 113400-36-5.mol
BOC-L-PYROGLUTAMIC ACID BENZYL ESTER Property
- Melting point:
- 69-70 °C
- Boiling point:
- 464.9±38.0 °C(Predicted)
- Density
- 1.219
- storage temp.
- 2-8°C
- pka
- -4.32±0.40(Predicted)
- form
- Powder
- color
- White
- InChI
- InChI=1S/C17H21NO5/c1-17(2,3)23-16(21)18-13(9-10-14(18)19)15(20)22-11-12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3/t13-/m0/s1
- InChIKey
- TZNBTMCEMLXYEM-ZDUSSCGKSA-N
- SMILES
- N1(C(OC(C)(C)C)=O)C(=O)CC[C@H]1C(OCC1=CC=CC=C1)=O
- CAS DataBase Reference
- 113400-36-5
Safety
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- J98391
- Product name
- Boc-Pyr-Obzl
- Packaging
- 25g
- Price
- $40
- Updated
- 2021/12/16
- Product number
- FB143703
- Product name
- (S)-2-Benzyl 1-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate
- Packaging
- 2g
- Price
- $75
- Updated
- 2021/12/16
- Product number
- FB143703
- Product name
- (S)-2-Benzyl 1-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate
- Packaging
- 5G
- Price
- $150
- Updated
- 2021/12/16
- Product number
- OR471630
- Product name
- Boc-L-PyroglutamicacidBenzylester
- Purity
- 98%
- Packaging
- 100g
- Price
- $179
- Updated
- 2021/12/16
- Product number
- FB143703
- Product name
- (S)-2-Benzyl 1-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate
- Packaging
- 10g
- Price
- $255
- Updated
- 2021/12/16
BOC-L-PYROGLUTAMIC ACID BENZYL ESTER Chemical Properties,Usage,Production
Uses
Boc-L-pyroglutamic acid benzyl ester is an intermediate in the synthesis of Avibactam, a novel non-beta-lactam β-lactamase inhibitor used in combination with ceftazidime for the treatment of complicated intra-abdominal infections, urinary tract infections, and pneumonia.
Synthesis
24424-99-5
94885-52-6
113400-36-5
General procedure for the synthesis of benzyl (S)-2-(tert-butyl) 5-oxopyrrolidine-1,2-dicarboxylate from di-tert-butyl dicarbonate and benzyl (S)-5-oxopyrrolidine-2-carboxylate: Benzyl (S)-5-oxopyrrolidine-2-carboxylate (8 g, 36.5 mmol, 1 equiv.) was dissolved in dichloromethane (150 mL). The mixture was stirred and cooled to 0°C. 4-Dimethylaminopyridine (DMAP, 4.9 g, 40.1 mmol, 1.1 eq.) and di-tert-butyl dicarbonate ((Boc)2O, 8.75 g, 40.1 mmol, 1.1 eq.) were added sequentially. The reaction mixture was slowly warmed to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction mixture was diluted with dichloromethane (250 mL) and washed sequentially with 1N aqueous hydrochloric acid (50 mL), saturated aqueous sodium bicarbonate (350 mL) and saturated aqueous sodium chloride. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to afford the target product (S)-benzyl 2-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate (8.6 g, 73.8% yield). lc-MS (ESI+, m/z = 656, [2M + NH4]+).
References
[1] Tetrahedron Letters, 2002, vol. 43, # 19, p. 3499 - 3501
[2] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 11, p. 2516 - 2525
[3] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 6, p. 507 - 514
[4] Tetrahedron, 2004, vol. 60, # 45, p. 10277 - 10284
[5] Patent: US2014/248242, 2014, A1. Location in patent: Paragraph 0402; 0404
BOC-L-PYROGLUTAMIC ACID BENZYL ESTER Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from BOC-L-PYROGLUTAMIC ACID BENZYL ESTER manufacturers
- Product
- Boc-L-Pyroglutamicacidbenzylester 113400-36-5
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1T+
- Release date
- 2023-10-11
- Product
- BOC-L-PYROGLUTAMIC ACID BENZYL ESTER 113400-36-5
- Price
- US $100.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- Customized
- Release date
- 2018-07-31