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CAS No.: | 113400-36-5 |
---|---|
Name: | BOC-L-PYROGLUTAMIC ACID BENZYL ESTER |
Article Data: | 27 |
Molecular Structure: | |
Formula: | C17H21NO5 |
Molecular Weight: | 319.357 |
Synonyms: | 1,2-Pyrrolidinedicarboxylic acid, 5-oxo-, 1-(1,1-dimethylethyl) 2-(phenylmethyl) ester, (S)-;2-Benzyl 1-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate;Benzyl N-Boc-pyroglutamate;(S)-5-Oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester; |
Density: | 1.22 g/cm3 |
Melting Point: | 69-70 °C |
Boiling Point: | 464.947 °C at 760 mmHg |
Flash Point: | 234.991 °C |
Appearance: | white crystalline powder |
PSA: | 72.91000 |
LogP: | 2.59380 |
di-tert-butyl dicarbonate
benzyl (L)-pyroglutamate
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0 - 20℃; | 98% |
With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; | 90% |
With dmap; triethylamine In dichloromethane at 0 - 23℃; for 17h; Inert atmosphere; | 90% |
di-tert-butyl dicarbonate
L-glutamic acid dibenzyl ester hydrochloride
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In toluene at 30 - 95℃; for 9h; Solvent; Temperature; Concentration; | 94.6% |
L-Pyroglutamic acid
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate
Conditions | Yield |
---|---|
94% | |
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 120 h / Heating 2: 9.0 g / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 384 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 85 percent / TEA / acetone 2: 73 percent / DMAP / acetonitrile View Scheme |
(2S,4S)-4-((R)-3-Methyl-1,1-dioxo-2,3-dihydro-1H-1λ6-benzo[d]isothiazol-3-yl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester
A
3-methylbenzo[d]isothiazole-1,1-dioxide
B
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran 1.) -78 deg C, 30 min, 2.) -78 deg C -> room temperature, 2 h; | A 40% B 38% |
methylmagnesium bromide
A
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate
B
benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxohexanoate
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene at -78℃; for 0.75h; Yield given. Yields of byproduct given; |
A
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate
B
benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxohexanoate
Conditions | Yield |
---|---|
With methylmagnesium bromide In tetrahydrofuran; toluene at -78℃; for 0.75h; Yield given. Yields of byproduct given; |
benzyl chloride
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 120 h / Heating 2: 9.0 g / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 384 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 120 h / 70 °C 2: triethylamine; dmap / dichloromethane / 16 h / 20 °C / Cooling with ice View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / acetone / 24 °C / Reflux; Inert atmosphere 2: dmap / dichloromethane / Inert atmosphere View Scheme |
benzyl chloride
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / TEA / acetone 2: 73 percent / DMAP / acetonitrile View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N,N-diisopropylethylamine / CH2Cl2 / 5 h / Heating 2: 37.5 g / 4-dimethylaminopyridine / acetonitrile / 3 h / 25 °C View Scheme |
benzyl bromide
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 88 percent / Et3N / acetone / 24 h / 20 °C 2: 90 percent / DIEA; DMAP / dimethylformamide / 3 h / 20 °C View Scheme |
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The Boc-L-Pyroglutamic acid benzyl ester, with the CAS registry number 113400-36-5, is also known as 2-Benzyl 1-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate. This chemical's molecular formula is C17H21NO5 and molecular weight is 319.35. What's more, its systematic name is 2-Benzyl 1-(2-methyl-2-propanyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate.
Physical properties of Boc-L-Pyroglutamic acid benzyl ester are: (1)ACD/LogP: 1.367; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.37; (4)ACD/LogD (pH 7.4): 1.37; (5)ACD/BCF (pH 5.5): 6.44; (6)ACD/BCF (pH 7.4): 6.44; (7)ACD/KOC (pH 5.5): 132.00; (8)ACD/KOC (pH 7.4): 132.00; (9)#H bond acceptors: 6 #H bond donors: 0; (10)#Freely Rotating Bonds: 6 ; (11)Polar Surface Area: 72.91 Å2; (12)Index of Refraction: 1.542; (13)Molar Refractivity: 82.397 cm3; (14)Molar Volume: 261.771 cm3; (15)Polarizability: 32.665×10-24cm3; (16)Surface Tension: 48.7369995117188 dyne/cm; (17)Density: 1.22 g/cm3; (18)Flash Point: 234.991 °C; (19)Enthalpy of Vaporization: 72.646 kJ/mol; (20)Boiling Point: 464.947 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC(C)(C)C)N2C(=O)CC[C@H]2C(=O)OCc1ccccc1
(2)Std. 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
(3)Std. InChIKey: TZNBTMCEMLXYEM-ZDUSSCGKSA-N