Boc-L-Pyroglutamic acid benzyl ester supplier

Name
BOC-L-PYROGLUTAMIC ACID BENZYL ESTER
EINECS
CAS No. 113400-36-5
Article Data27
CAS DataBase
Density 1.22 g/cm³
Solubility
Melting Point 69-70 °C
Formula C₁₇H₂₁NO₅
Boiling Point 464.947 °C at 760 mmHg
Molecular Weight 319.357
Flash Point 234.991 °C
Transport Information
Appearance white crystalline powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 72.91000
LogP 2.59380

Synthetic route

: 24424-99-5
di-tert-butyl dicarbonate

: 94885-52-6
benzyl (L)-pyroglutamate

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

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%

: 24424-99-5
di-tert-butyl dicarbonate

: 4561-10-8
L-glutamic acid dibenzyl ester hydrochloride

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene at 30 - 95℃; for 9h; Solvent; Temperature; Concentration;	94.6%

: 98-79-3
L-Pyroglutamic acid

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

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

: 135347-23-8
(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: 34989-82-7
3-methylbenzo[d]isothiazole-1,1-dioxide

B: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

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%

: 75-16-1
methylmagnesium bromide

: (S)-2-tert-Butoxycarbonylamino-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

A: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

B: 113400-46-7
benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxohexanoate

Conditions

Conditions	Yield
In tetrahydrofuran; toluene at -78℃; for 0.75h; Yield given. Yields of byproduct given;

...Expand

: (S)-2-tert-Butoxycarbonylamino-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

A: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

B: 113400-46-7
benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxohexanoate

Conditions

Conditions	Yield
With methylmagnesium bromide In tetrahydrofuran; toluene at -78℃; for 0.75h; Yield given. Yields of byproduct given;

: 100-44-7
benzyl chloride

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

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

: 100-44-7
benzyl chloride

N,N-diethyl-glycine-<4-hydroxy-anilide>: N,N-diethyl-glycine-<4-hydroxy-anilide>

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / TEA / acetone 2: 73 percent / DMAP / acetonitrile View Scheme

: 100-39-0
benzyl bromide

(1R,2R)-O-Merrifield bound N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2'-phenylacetamide: (1R,2R)-O-Merrifield bound N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2'-phenylacetamide

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

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

: 100-39-0
benzyl bromide

XOOC-CH2-COOX: XOOC-CH2-COOX

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

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

: 98-79-3
L-Pyroglutamic acid

Fmoc-Pro-Rink amide-MBHA resin: Fmoc-Pro-Rink amide-MBHA resin

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

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
Multi-step reaction with 2 steps 1: 90 percent / SOCl2; DMF / 20 °C 2: 98 percent / dimethylaminopyridine / CH2Cl2 / 0 - 20 °C View Scheme

: 100-51-6
benzyl alcohol

BocNH-C(=NBoc)-SCH2-terminated resin: BocNH-C(=NBoc)-SCH2-terminated resin

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / SOCl2; DMF / 20 °C 2: 98 percent / dimethylaminopyridine / CH2Cl2 / 0 - 20 °C View Scheme

: 100-51-6
benzyl alcohol

NaCpW(CO)3: NaCpW(CO)3

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / SOCl2 / 0 - 20 °C 2: Et3N; DMAP View Scheme

: 100-39-0
benzyl bromide

t-BuOCOCH2-X: t-BuOCOCH2-X

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: DIEA / CH2Cl2 / Heating 2: 9.56 g / DMAP; Et3N / acetonitrile / 20 °C View Scheme

: 30924-93-7
Boc-Glu-OBn

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 4-methylmorpholine / CH2Cl2 / 0.25 h / 0 °C 2: tetrahydrofuran; toluene / 0.75 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1: 4-methylmorpholine / CH2Cl2 / 0.25 h / 0 °C 2: methylmagnesium bromide / tetrahydrofuran; toluene / 0.75 h / -78 °C View Scheme

: 100-44-7
benzyl chloride

sodium-compound of 1-cyclopentyl-ethanone: sodium-compound of 1-cyclopentyl-ethanone

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NEt3 / tetrahydrofuran / 120 h / Heating 2: NEt3 / CH2Cl2 View Scheme

: 100-44-7
benzyl chloride

hydroxylamine hydrochloride: hydroxylamine hydrochloride

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / triethylamine / acetone / 168 h / Heating 2: 75 percent / DMAP / acetonitrile / 1.) 0 deg C, 2 h, 2.) r.t., overnight View Scheme

: 34619-03-9
tert-butyldicarbonate

: 94885-52-6
benzyl (L)-pyroglutamate

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
With dmap In dichloromethane at 20℃; for 4h;

: 100-51-6
benzyl alcohol

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / N,N-dimethyl-formamide / 0 - 20 °C 2: dmap / dichloromethane / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 16 h / 0 - 23 °C / Inert atmosphere 2: dmap; triethylamine / dichloromethane / 17 h / 0 - 23 °C / Inert atmosphere View Scheme

: 100-44-7
benzyl chloride

: 98-79-3
L-Pyroglutamic acid

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; potassium iodide / toluene / 80 °C 2: 4-pyrrolidin-1-ylpyridine / 50 °C View Scheme

: 100-39-0
benzyl bromide

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / acetone / 16 h / Reflux 2: dmap; triethylamine / dichloromethane / 16 h / 50 °C / Inert atmosphere View Scheme

: 1774-47-6
trimethylsulfoxonium iodide

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: benzyl (2S)-2-((tert-butoxycarbonyl)amino)-6-(dimethyl(oxo)-λ6-sulfanylidene)-5-oxohexanoate

Conditions

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 1h; Stage #2: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran; dimethyl sulfoxide at -10℃;	100%
With potassium carbonate In dimethyl sulfoxide at 50℃; for 23h; Temperature; Reagent/catalyst; Solvent;	96%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at 20℃; Stage #2: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran; dimethyl sulfoxide at -12℃;
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate; dimethyl sulfoxide In tetrahydrofuran at 25℃; for 1h; Large scale; Industrial scale; Stage #2: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran at -12℃; Large scale; Industrial scale;
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at 25℃; for 2h; Stage #2: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran; dimethyl sulfoxide at 0 - 10℃; for 8h;

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 331949-29-2
benzyl (2S)-N-tert-butoxycarbonyl-5-hydroxypyrrolidine-2-carboxylate

Conditions

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran at -78℃; for 2h;	99%
With lithium triethylborohydride In tetrahydrofuran at -78℃; for 0.5h;	95%
With lithium triethylborohydride In tetrahydrofuran at -78℃; for 2h;	88%
With diisobutylaluminium hydride In tetrahydrofuran at -78℃;	70%
With lithium triethylborohydride In tetrahydrofuran at -78℃;

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 53100-44-0
L-N-t-butoxycarbonylpyroglutamic acid

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate for 120h; Ambient temperature;	98%
With hydrogen; 10percent Pd/C In ethyl acetate under 2280.15 Torr; for 1h;	98%
With hydrogen; palladium on activated charcoal In methanol for 6h;	93%

: 67-56-1
methanol

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 331949-31-6
benzyl (2S)-N-tert-butoxycarbonyl-5-methoxypyrrolidine-2-carboxylate

Conditions

Conditions	Yield
Stage #1: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate With diisobutylaluminium hydride In tetrahydrofuran at -78℃; Stage #2: methanol With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; Further stages.;	95%
Stage #1: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate With lithium triethylborohydride In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: With dihydrogen peroxide In tetrahydrofuran; water at -78 - 20℃; Inert atmosphere; Stage #3: methanol With toluene-4-sulfonic acid In water at 20℃; Inert atmosphere; chemoselective reaction;	86%

: 399-94-0
2-bromo-1,4-difluorobenzene

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: C23H25F2NO5

Conditions

Conditions	Yield
Stage #1: 2-bromo-1,4-difluorobenzene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 2h; Stage #2: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran at 0℃; for 4h;	93%

: 32359-01-6
hexenylmagnesium bromide

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 113400-48-9
(S)-2-tert-Butoxycarbonylamino-5-oxo-undec-6-ynoic acid benzyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at -40℃; for 2h;	92%

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 91229-97-9
(S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

Conditions

Conditions	Yield
With sodium tetrahydroborate; potassium dihydrogenphosphate In methanol; water at 0℃; for 1.5h; Reduction;	92%
With sodium tetrahydroborate; water In tetrahydrofuran at 0 - 23℃; for 2h; Inert atmosphere;	49%
With sodium tetrahydroborate; potassium dihydrogenphosphate In methanol; water at 0℃; for 2h;	12%

: 917-54-4
methyllithium

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 113400-46-7
benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxohexanoate

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78 - 20℃; for 2h; Inert atmosphere;	91%

: 24424-99-5
di-tert-butyl dicarbonate

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 91229-91-3
tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

Conditions

Conditions	Yield
Stage #1: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate With hydrogen; palladium on activated charcoal In ethyl acetate Stage #2: di-tert-butyl dicarbonate With dmap; TEA In acetonitrile Further stages.;	83%
With dmap; hydrogen; triethylamine 2.) CH3CN; Multistep reaction;

: 1826-67-1
vinyl magnesium bromide

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 113400-37-6
2-tert-butoxycarbonylamino-5-oxo-hept-6-enoic acid benzyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at -40℃; for 2h;	82%

: 917-64-6
methyl magnesium iodide

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 113400-46-7
benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxohexanoate

Conditions

Conditions	Yield
In tetrahydrofuran at -40℃; for 2h;	78%

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 591-51-5
phenyllithium

: 148626-26-0
(S)-2-tert-Butoxycarbonylamino-5-oxo-5-phenyl-pentanoic acid benzyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at -40℃; for 2h;	77%

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 756-79-6
dimethyl methane phosphonate

: 270585-72-3
(2S)-α-benzyl 2-N-(tert-butyloxycarbonyl)amino-5-oxo-6-(dimethylphosphonyl)hexanoate

Conditions

Conditions	Yield
Stage #1: dimethyl methane phosphonate With n-butyllithium In toluene at -78℃; for 0.333333h; Metallation; Stage #2: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In toluene at -78 - 20℃; Addition; Further stages.;	74%

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 18107-18-1
diazomethyl-trimethyl-silane

: 208519-99-7
(S)-2-tert-Butoxycarbonylamino-6-diazo-5-oxo-hexanoic acid benzyl ester

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -105 - -100℃; for 0.166667h;	71%

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 1730-25-2
allylmagnesium bromide

: 113400-47-8
(S)-2-tert-Butoxycarbonylamino-5-oxo-oct-7-enoic acid benzyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at -40℃; for 2h;	70%

: 100-39-0
benzyl bromide

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 1243255-28-8
2-benzyl 1-(tert-butyl) (2S)-4-benzyl-5-oxo-1,2-pyrrolidinedicarboxylate

Conditions

Conditions	Yield
Stage #1: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.08333h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran at -78℃; for 16.05h; Inert atmosphere; stereoselective reaction;	69%

: 81290-20-2
(trifluoromethyl)trimethylsilane

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: N-Boc-5-trifluoromethyl-5-trimethylsilyloxy-L-proline benzyl ester

Conditions

Conditions	Yield
With cesium fluoride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	66%

: 33797-51-2
eschenmoser's salt

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 159829-96-6
(S)-4,4-Bis-dimethylaminomethyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.666667h;	65%

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 74-88-4
methyl iodide

: (2S,4R)-4-methyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

Conditions

Conditions	Yield
Stage #1: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate With lithium hexamethyldisilazane In tetrahydrofuran at -80℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at -80 - 20℃;	64.9%

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 94885-52-6
benzyl (L)-pyroglutamate

Conditions

Conditions	Yield
With trimethylaluminum In dichloromethane Ambient temperature;	64%

: 7103-09-5
4-but-1-enylmagnesium bromide

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 1282532-98-2
(S)-2-tert-butoxycarbonylamino-5-oxo-non-8-enoic acid benzyl ester

Conditions

Conditions	Yield
Stage #1: 4-but-1-enylmagnesium bromide; benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran at -40℃; for 3h; Stage #2: With ammonium chloride In tetrahydrofuran; water	62%
Stage #1: 4-but-1-enylmagnesium bromide; benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate In tetrahydrofuran at -40℃; for 3h; Stage #2: With water; ammonium chloride In tetrahydrofuran	62%

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 79-22-1
methyl chloroformate

: 5-oxo-pyrrolidine-1,2,4-tricarboxylic acid 2-benzyl ester 1-tert-butyl ester 4-methyl ester

Conditions

Conditions	Yield
Stage #1: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Stage #2: methyl chloroformate In tetrahydrofuran at -78℃; for 3h;	60%

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 870-63-3
prenyl bromide

: 1243255-29-9
2-benzyl 1-(tert-butyl) (2S)-4-(3-methyl-2-butenyl)-5-oxo-1,2-pyrrolidinedicarboxylate

Conditions

Conditions	Yield
Stage #1: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.08333h; Inert atmosphere; Stage #2: prenyl bromide In tetrahydrofuran at -78℃; for 16.05h; Inert atmosphere; stereoselective reaction;	60%

: 96090-12-9, 124854-99-5
1-(4-bromophenyl)-1-propen-3-yl bromide

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

A: benzyl (2S,4R,E)-N-BOC-4-(4-bromocinnamyl)pyroglutamate

B: benzyl (2S,4S,E)-N-BOC-4-(4-bromocinnamyl)pyroglutamate

Conditions

Conditions	Yield
Stage #1: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Activation; Stage #2: 1-(4-bromophenyl)-1-propen-3-yl bromide In tetrahydrofuran at -78℃; for 2h; Alkylation;	A 58% B n/a
Stage #1: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Substitution; Stage #2: 1-(4-bromophenyl)-1-propen-3-yl bromide In tetrahydrofuran at -78℃; for 2h; Alkylation;	A 58% B n/a

...Expand

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 116857-24-0
benzyl (2S,4R)-1-tert-butoxycarbonyl-4-hydroxy-5-oxopyrrolidine-2-carboxylate

Conditions

Conditions	Yield
Stage #1: benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: With N-(benzenesulfonyl)-3-phenyloxaziridine In tetrahydrofuran at -78℃; for 0.75h; Stage #3: With camphor-10-sulfonic acid; water In tetrahydrofuran at -78 - 20℃; stereoselective reaction;	55%
With 2-toluenesulfonyl-3-phenyloxazolidine; lithium hexamethyldisilazane 1.) THF, -78 deg C; Yield given. Multistep reaction;

: 4224-69-5
methyl 2-(bromomethyl)propenoate

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

A: benzyl (2S,4S)-N-tert-butoxycarbonyl-4-(2-carboxymethylprop-2-enyl)pyroglutamate

B: benzyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-carboxymethylprop-2-enyl)pyroglutamate

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Yields of byproduct given;	A 54% B n/a
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

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lithium hexamethydisilylazide: lithium hexamethydisilylazide

: 113400-36-5
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

: 4392-24-9
Cinnamyl bromide

: 220424-73-7
Boc-4(R)-(3-phenylpropyl)proline

Conditions

Conditions	Yield
With ammonium chloride In tetrahydrofuran	54%

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Boc-L-Pyroglutamic acid benzyl ester Specification

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

Product Name

BOC-L-PYROGLUTAMIC ACID BENZYL ESTER

Synthetic route

Boc-L-Pyroglutamic acid benzyl ester Specification

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