ChemicalBook > CAS DataBase List > BOC-L-PYROGLUTAMIC ACID BENZYL ESTER

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
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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
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Safety

HS Code 
2933998090
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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.

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N-Bromosuccinimide Price

AK Scientific
Product number
J98391
Product name
Boc-Pyr-Obzl
Packaging
25g
Price
$40
Updated
2021/12/16
Biosynth Carbosynth
Product number
FB143703
Product name
(S)-2-Benzyl 1-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate
Packaging
5G
Price
$150
Updated
2021/12/16
Apolloscientific
Product number
OR471630
Product name
Boc-L-PyroglutamicacidBenzylester
Purity
98%
Packaging
100g
Price
$179
Updated
2021/12/16
AK Scientific
Product number
J98391
Product name
Boc-Pyr-Obzl
Packaging
500g
Price
$473
Updated
2021/12/16
Biosynth Carbosynth
Product number
FB143703
Product name
(S)-2-Benzyl 1-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate
Packaging
25g
Price
$510
Updated
2021/12/16
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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

Sichuan HongRi Pharma-Tech Co.,Ltd
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
Career Henan Chemical Co
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

113400-36-5, BOC-L-PYROGLUTAMIC ACID BENZYL ESTERRelated Search:

(2S,4S)-1-(tert-butoxycarbonyl)-4-(MethoxyMethyl)pyrrolidine-2-carboxylic acid N-BOC-CIS-4-CYANO-L-PROLINE METHYL ESTER Velpatasvir intermediate Velpatasvir Velpatasvir intermediate Velpatasvir intermediate (R)-2-(methoxycarbonylamino)-2-phenylacetic acid Velpatasvir Co Povidone Velpatasvir intermediate (2S,5S)-1-((methoxycarbonyl)-L-valyl)-5-methylpyrrolidine-2-carboxylic acid Velpatasvir-A12

  • BOC-L-PYROGLUTAMIC ACID BENZYL ESTER
  • (2R)-5-Oxo-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) 2-(phenylmethyl) ester
  • Boc-PyroglutaMic acid. Benzyl ester
  • Boc-Pyr-Obzl
  • (S)-2-Benzyl 1-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate
  • Benzyl (S)-1-Boc-5-oxopyrrolidine-2-carboxylate, 98%
  • 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, 1-(1,1-diMethylethyl)2-(phenylMethyl) ester, (S)-
  • 2-O-benzyl 1-O-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate
  • (Tert-Butoxy)Carbonyl Pyr-OBzl
  • 2-benzyl 1-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate
  • PYR294
  • 2-benzyl1-(tert-butyl)(S)-5-oxopyrrolidine-1,2-dicarboxylate
  • (2S)-benzyl N-(tert-butyloxycarbonyl)-pyroglutamate
  • 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, 1-(1,1-dimethylethyl) 2-(phenylmethyl) ester, (2S)-
  • Benzyl(S)-1-Boc-5-oxopyrrolidine-2-carboxylate,98%
  • N-BOC-L-Pyroglutamic acid benzyl ester
  • BOC-L-PYROGLUTAMIC ACID BENZYL ESTER USP/EP/BP
  • T-butoxycarbonyl-l-pyroglutamic acid benzyl ester
  • 2-benzyl 1-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylat...
  • Boc-l-pyroglutamate benzyl ester
  • 1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate
  • Boc-Pyr-Obzl-OH
  • N-tert-Butoxycarbonyl-L-pyroglutamic acid Benzyl ester
  • 113400-36-5