N-Carbobenzyloxy-L-valine supplier

Name
N-Carbobenzyloxy-L-valine
EINECS 214-562-1
CAS No. 1149-26-4
Article Data91
CAS DataBase
Density 1.182 g/cm³
Solubility
Melting Point 62-64 °C(lit.)
Formula C₁₃H₁₇NO₄
Boiling Point 432.6 °C at 760 mmHg
Molecular Weight 251.282
Flash Point 215.4 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 36/37-36-26
Risk Codes 38-43-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms N-Carbobenzoxyvaline;N-Cbz-L-Valine;Z-Val-OH;N-CBZ-L-Val-OH;Valine,N-carboxy-, N-benzyl ester, L- (8CI);(+)-N-[(Phenylmethoxy)carbonyl]-L-valine;(2S)-2-[(Benzyloxycarbonyl)amino]-3-methylbutanoic acid;(S)-2-[(Benzyloxycarbonyl)amino]-3-methylbutanoic acid;Benzyloxycarbonyl-L-valine;CBZ-L-valine;Carbobenzoxy-L-valine;N-(Benzyloxycarbonyl)-L-valine;N-(Benzyloxycarbonyl)valine;N-Benzyloxycarbonyl-(S)-valine;
PSA 75.63000
LogP 2.41290

Synthetic route

: 72-18-4
L-valine

: 501-53-1
benzyl chloroformate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water Inert atmosphere;	100%
With sodium hydroxide In water at 0 - 20℃;	100%
With potassium carbonate In water at 0 - 2℃; pH=1.5 - Ca. 2; Reagent/catalyst; pH-value; Temperature; Solvent;	99%

: 1431461-34-5
C13H15N2O2(1+)*CF3O3S(1-)

: 1428647-69-1
(L)-valine methyl ester triflate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
Stage #1: C13H15N2O2(1+)*CF3O3S(1-); (L)-valine methyl ester triflate With 1,1’-carbonylbis-(3-ethylimidazolium) triflate In nitromethane at 20℃; for 60h; Inert atmosphere; Stage #2: With water; sodium hydroxide In nitromethane at 20℃; for 2h; Inert atmosphere;	80%

: 6216-65-5
N-benzyloxycarbonyl-L-valinol

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With 2-hydroxypyridin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 72h;	79%

: (S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid 3-methyl-but-2-enyl ester

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With cerium(III) chloride; sodium iodide In acetonitrile for 2h; Heating;	92%
With sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 5h;	91%
With sodium iodide; zirconium(IV) chloride In acetonitrile for 2h; Heating;	91%

: 394210-42-5
4-isopropyl-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
Stage #1: 4-isopropyl-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester With methanol; 4 A molecular sieve In diethyl ether at 0℃; for 22h; Stage #2: With water Further stages.;	40%

: 16874-02-5
benzyl (S)-1-(tert-butoxycarbonyl)-2-methylpropylcarbamate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 1.08333h;

: DL-Val/PyS

: 501-53-1
benzyl chloroformate

A: 1685-33-2
N-[(benzyloxy)carbonyl]-D-valine

B: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
Stage #1: DL-Val/PyS With alpha cyclodextrin In ethanol; dimethyl sulfoxide at 30℃; for 24h; Stage #2: benzyl chloroformate

...Expand

: 78031-88-6
(S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid 2,2-dibromo-1-tert-butylcarbamoyl-propyl ester

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With sodium metaborate; cobalt(II) phthalocyanine In ethanol at 20℃; for 1h;	64%

: 122665-04-7
(S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid allyl ester

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With morpholine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 30℃; for 12h;	79%

: 17498-50-9, 25616-14-2, 31320-20-4
L-valine hydrochloride

: 501-53-1
benzyl chloroformate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 16h; Solvent; Temperature;

: 24210-19-3
methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With 2C33H37N*H2O7S2; water at 80℃; for 9h; optical yield given as %ee;	86%
With sodium hydroxide In methanol

: 140-89-6
potassium ethyl xanthogenate

: 210578-20-4
(S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid 5-methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indol-3-ylmethyl ester

A: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

B: Dithiocarbonic acid O-ethyl ester S-(5-methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indol-3-ylmethyl) ester

Conditions

Conditions	Yield
With sodium dithionite In tetrahydrofuran; water	A 67% B 72%

...Expand

: 13139-17-8
N-(Benzyloxycarbonyloxy)succinimide

: 72-18-4
L-valine

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane; water at 0℃;
With sodium hydrogencarbonate In acetone at 20℃;

: 72-18-4
L-valine

: 91285-92-6
N-(benzyloxycarbonyl)benzothiazolin-2-thione

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane for 12h; Ambient temperature;	90%

: 72-18-4
L-valine

: 91285-93-7
1-Benzyloxycarbonylbenzimidazoline-2-thione

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane for 12h; Ambient temperature;	91%

: 72-18-4
L-valine

: dimethylsulfonium methyl sulfate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With triethylamine In water Ambient temperature;	82%

: 501-53-1
benzyl chloroformate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / Et3N / acetonitrile / 2 h / 5 °C 2: 82 percent / Et3N / H2O / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 89 percent / quinoline; CH2Cl2 / 12 h / Ambient temperature 2: 74 percent / triethylamine; CHCl3; H2O / 18 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 38 percent / NaHCO3 / CH2Cl2; H2O / Ambient temperature 2: Jones' reagent / acetone / 3 h / 0 °C View Scheme

: 72-18-4
L-valine

: 91285-94-8
O-benzyl S-(pyridin-2-yl)carbonothioate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane for 12h; Ambient temperature;	82%

: 72-18-4
L-valine

: 91285-91-5
benzyl 2-thioxobenzo[d]oxazol-3(2H)-carboxylate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane for 12h; Ambient temperature;	81%

: 2816-12-8, 24601-74-9
4-isopropyl-2,5-oxazolidinedione

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NMM / tetrahydrofuran / -25 - 20 °C 2.1: 20 mol percent DHQD-PHN; 4 Angstroem molecular sieves; methanol / diethyl ether / 22 h / 0 °C 2.2: 40 percent / H2O View Scheme

: Z-L-Val p-chlorophenyl ester

A: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

B: 106-48-9
4-chloro-phenol

Conditions

Conditions	Yield
With thiolsubtilisin In water; N,N-dimethyl-formamide Ambient temperature; pH 8.0 phosphate buffer containing PhB(OH)2 traces;

: 10466-61-2
(2S)-amino-4-methylpentanamide hydrochloride

: 203640-53-3
Z-L-Val carbamoylmethyl ester

A: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

B: 95303-78-9
Z-L-Val-L-Leu-NH2

Conditions

Conditions	Yield
With α-chymotripsin on Celite; Tris buffer; TEA In acetonitrile at 30℃; for 48h;	A 6.8% B 13.6%

...Expand

: 20194-18-7
sodium phenyl-methanolate

A: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

B S-benzyl-L-cysteine benzyl ester-toluene-4-sulfonate: S-benzyl-L-cysteine benzyl ester-toluene-4-sulfonate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / tetrahydrofuran / 6 h / 30 °C 2: aq. NaOH / methanol View Scheme
Multi-step reaction with 2 steps 1: 72 percent / tetrahydrofuran / 6 h / 30 °C 2: 79 percent / DBU, morpholine / Pd(dba)2, PPh3 / acetonitrile / 12 h / 30 °C View Scheme

: 192930-84-0
(S)-N-[Bis(methylthio)methylene]valine allyl ester

A: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

B S-benzyl-L-cysteine benzyl ester-toluene-4-sulfonate: S-benzyl-L-cysteine benzyl ester-toluene-4-sulfonate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / tetrahydrofuran / 6 h / 30 °C 2: 79 percent / DBU, morpholine / Pd(dba)2, PPh3 / acetonitrile / 12 h / 30 °C View Scheme

: 21844-69-9
picolyl N-Cbz-L-valinate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With magnesium In methanol at 20℃; for 4h;

: 6216-65-5
N-benzyloxycarbonyl-L-valinol

A: 1685-33-2
N-[(benzyloxy)carbonyl]-D-valine

B: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With jones' reagent In acetone at 0℃; for 3h; Yield given. Yields of byproduct given;

: 10512-93-3
Z-Val-ONp

A: 100-02-7
4-nitro-phenol

B: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
With cetyltrimethylammonim bromide; Dec-L-His In acetonitrile at 25℃; Rate constant; 0.02M phosphate buffer, pH=7.3; other catalysts;
With papain (preactivated with 2E-3M ethylenediaminotetraacetic acid (tetrasodium salt) and 5E-3M L-cysteine); water In acetonitrile at 21℃; Kinetics; pH=3.4-4.0 (formate and acetate buffers); pre-steady-state and steady-state parameters describing papain action;
With water at 21℃; Rate constant; Mechanism; pH dependence of the rate constant and catalytic effect of amino acid;

: 72-18-4
L-valine

: 96452-48-1
benzyl pyridin-2-yl carbonate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
In chloroform; water; triethylamine for 18h; Ambient temperature;	74%

: 100-51-6
benzyl alcohol

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) NaH / 1) THF, reflux, 2h, 2) room temperature, 1h 2: tetrahydrofuran / 3 h / Ambient temperature 3: 92 percent / standard pH stat conditions View Scheme

: 72-18-4
L-valine

: dibenzyl pyrocarbonate

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

Conditions

Conditions	Yield
standard pH stat conditions;	92%

: 186581-53-3, 908094-01-9
diazomethane

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 24210-19-3
methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate

Conditions

Conditions	Yield
In diethyl ether	100%
With diethyl ether

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 87052-60-6
Z-(L)-Val-Cl

Conditions

Conditions	Yield
With oxalyl dichloride In chloroform; N,N-dimethyl-formamide at 20℃; for 5h; Cooling with ice; Reflux;	100%
With diethyl ether; phosphorus pentachloride
With thionyl chloride In N,N,N,N,N,N-hexamethylphosphoric triamide; acetonitrile at -5 - 0℃; for 0.25h;

: 4070-48-8
L-Valine methyl ester

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 1999-88-8
methyl (S)-2-((S)-2-benzyloxycarbonyl-amino-3-methylbutyrylamino)-3-methylbutyrate

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 20℃;	100%
With N-ethyl-N,N-diisopropylamine; <4-nitro-6-(trifluoromethyl)benzotriazol-1-yloxy>tris(pyrrolidino)phosphonium hexafluorophosphate at 20℃; for 1h;	98%
With 3,3'-Dicyano-4,4',6,6'-tetramethyl-2,2'-dipyridinyl-disulfid; triphenylphosphine In dichloromethane at -20 - -15℃; for 12h;	84%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 3339-44-4
methyl N-methyl-L-valinate hydrochloride

: 128892-28-4
N--L-N-methylvaline methyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane 1) 1 min in the cold, 2) 1 h at r.t.; other coupling reagents;	100%
With N-ethyl-N,N-diisopropylamine; chlorotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate In dichloromethane for 3h; Ambient temperature;	96%
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane 1.) 0 deg C, 1 min, 2.) r.t., 3 h;	90%
With bromo-tris-dimethylamino-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Ambient temperature;	71%
With N-ethyl-N,N-diisopropylamine; <6-(trifluoromethyl)benzotriazol-1-yloxy>tris(dimethylamino)phosphonium hexafluorophosphate In dichloromethane at 35℃; for 1h;	49%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 155336-09-7
(2S,3S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-butane-1,4-diol

: (S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid (2S,3S)-4-((S)-2-benzyloxycarbonylamino-3-methyl-butyryloxy)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-butyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 24h; Ambient temperature;	100%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 6216-65-5
N-benzyloxycarbonyl-L-valinol

Conditions

Conditions	Yield
Stage #1: (S)-N-(benzyloxycarbonyl)valine With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.25h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at -15℃; for 1h;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃;
Multi-step reaction with 2 steps 1: DCC / ethyl acetate / 20 h / 20 °C 2: NaBH4; AcOH / methanol; dioxane View Scheme

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 100-46-9
benzylamine

: 20998-83-8
(S)-benzyl (1-(benzylamino)-3-methyl-1-oxobutan-2-yl)carbamate

Conditions

Conditions	Yield
With N,N'-Bis(2-oxo-3-oxazolidinyl)phosphorodiamidic azide; triethylamine In dichloromethane	100%
Stage #1: (S)-N-(benzyloxycarbonyl)valine With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.75h; Stage #2: benzylamine at 0 - 20℃; for 17h;	89%
With triethylamine; isobutyl chloroformate In tetrahydrofuran for 16h; Ambient temperature;

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 188476-28-0
(R)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxypropanoic acid methyl ester

: (S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid (R)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-propyl ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃;	100%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: (1R,2S)-1-tert-Butoxycarbonylamino-2-hydroxy-cyclohexanecarboxylic acid methyl ester

: 209127-52-6
(1R,2S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyryloxy)-1-tert-butoxycarbonylamino-cyclohexanecarboxylic acid methyl ester

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃;	100%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 120-20-7
2-(3,4-dimethoxyphenyl)-ethylamine

: 143491-22-9
benzyl (1S)-1-({[2-(3,4-dimethoxyphenyl)ethyl]amino}carbonyl)-2-methylpropylcarbamate

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20℃;	100%
With 1,1'-carbonyldiimidazole In tetrahydrofuran; dichloromethane

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 672912-23-1
N4-(4-ethyl-6-methoxy-5-propoxy-quinolin-8-yl)-pentane-1,4-diamine

: {(S)-1-[4-(4-Ethyl-6-methoxy-5-propoxy-quinolin-8-ylamino)-pentylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;	100%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 672912-26-4
N4-(4-ethyl-5-hexyloxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine

: {(S)-1-[4-(4-Ethyl-5-hexyloxy-6-methoxy-quinolin-8-ylamino)-pentylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;	100%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: Dimethyl-(3-methyl-2-butenyl)-sulfonium tetrafluoroborate

: Cbz-Val-OH 1,1-dimethylallyl ester

Conditions

Conditions	Yield
With potassium carbonate; copper(I) bromide In dichloromethane at 20℃;	100%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: (2R,3R,11bR)-dihydrotetrabenazine

: 1025504-76-0
(S)-2-benzyloxycarbonyl-amino-3-methylbutyric acid-(2R,3R,11bR)-3-isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl ester

Conditions

Conditions	Yield
Stage #1: (2R,3R,11bR)-dihydrotetrabenazine With dmap In dichloromethane Stage #2: (S)-N-(benzyloxycarbonyl)valine In dichloromethane for 0.0833333h; Stage #3: With dicyclohexyl-carbodiimide In dichloromethane	100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane	95.7 g

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 178113-56-9
L-2-hydroxy-3-methylbutanoic acid allyl ester

: C21H29NO6

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	100%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 623-33-6
glycine ethyl ester hydrochloride

: 2766-17-8
ethyl N-(benzyloxycarbonyl)-L-valylglycinate

Conditions

Conditions	Yield
With 3,3'-(phenylphosphinylidene)bis<2(3H)-benzothiazolone; triethylamine In dichloromethane for 2h; Ambient temperature;	99%
With TEA; diphenyl (2,3-dihydro-2-thioxo-3-benzoxazolyl)phosphonate In dichloromethane for 2h; Ambient temperature;	99%
With TEA; 1,2-benzisoxazol-3-yl diphenyl phosphate In dichloromethane for 2h; Ambient temperature;	95%

: 2666-93-5
(S)-Leu-OMe

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 4817-93-0
(S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-4-methylpentanoate

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane	99%
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 3519-30-0
L-α-hydroxyisovaleric acid t-butyl ester

: 13516-17-1
benzyloxycarbonyl-L-valyl-L-α-hydroxyisovaleric acid t-butyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 24h; Ambient temperature;	99%
(i) PhSO2Cl, Py, (ii) /BRN= 4658890/; Multistep reaction;

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 5557-81-3, 5557-83-5, 34404-37-0
L-alanine benzyl ester hydrochloride

: 118234-89-2
Z-(S)-Val-(S)-Ala-OBzl

Conditions

Conditions	Yield
With TEA; diphenyl (2,3-dihydro-2-thioxo-3-benzoxazolyl)phosphonate In dichloromethane for 2h; Ambient temperature;	99%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 96935-01-2
Isopropenyl Succinimido Carbonate

: 3496-11-5
2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate

Conditions

Conditions	Yield
With dmap In acetonitrile for 4h; Ambient temperature;	99%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 137283-63-7
Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester isopropenyl ester

: 53666-01-6
N-(benzyloxycarbonyl)-L-valine N-hydroxy-5-norbornene-2,3-dicarboximide ester

Conditions

Conditions	Yield
With dmap In acetonitrile for 4h; Ambient temperature;	99%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 114744-84-2
Nα-(benzyloxycarbonyl)-N-methoxy-N-methyl-L-valinamide

Conditions

Conditions	Yield
Stage #1: (S)-N-(benzyloxycarbonyl)valine With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In ethyl acetate; acetonitrile at 0℃; for 0.166667h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In ethyl acetate; acetonitrile at 0℃; for 0.5h;	99%
Stage #1: (S)-N-(benzyloxycarbonyl)valine With triethylamine; HATU In dichloromethane at 20℃; for 0.25h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃;	85.4%
Stage #1: (S)-N-(benzyloxycarbonyl)valine With triethylamine; HATU In dichloromethane at 20℃; for 0.25h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃;	85.4%

: 1190207-25-0
(S)-N-tert-butoxycarbonyl-2-[bis(2-methylphenyl)phosphinomethyl]pyrrolidine

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: benzyl N-{1-(R)-[(2-(S)-bis(2-methylphenyl)phosphinomethyl)pyrrolidine-1-carbonyl]-2-methylpropyl}carbamate

Conditions

Conditions	Yield
Stage #1: (S)-N-tert-butoxycarbonyl-2-[bis(2-methylphenyl)phosphinomethyl]pyrrolidine With hydrogenchloride In 1,4-dioxane at 0 - 20℃; Inert atmosphere; Stage #2: (S)-N-(benzyloxycarbonyl)valine With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at -20 - 20℃; for 19.5h;	99%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 52663-90-8
1-(2',3'-di-O-isopropylidene-β-D-ribofuranosyl)<1,2,4>triazole-3-carboxamide

: C24H31N5O8

Conditions

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	99%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 7517-19-3
methyl (L)-leucinate hydrochloride

: 4817-93-0
(S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanamido)-4-methylpentanoate

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	99%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	69%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 13139-28-1
(S)-N-benzyloxycarbonylvalinamide

Conditions

Conditions	Yield
Stage #1: (S)-N-(benzyloxycarbonyl)valine With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: With ammonium chloride In N,N-dimethyl-formamide at 23℃; for 16h;	98%
Stage #1: (S)-N-(benzyloxycarbonyl)valine With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With ammonium chloride In tetrahydrofuran; water at 0℃; for 0.5h;	93%
With hexamethylphosphorous triamide dichloride; ammonia In dichloromethane 1) 30 min, -20 deg C, 2) 4 h, r.t.;	87.5%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 39809-25-1
Penciclovir

: (S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid 4-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-((S)-2-benzyloxycarbonylamino-3-methyl-butyryloxymethyl)-butyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 32h; Ambient temperature;	98%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 108-68-9
3,5-Dimethylphenol

: 619337-54-1
N-benzyloxycarbonyl-L-valine 3,5-dimethylphenyl ester

Conditions

Conditions	Yield
With 4-methyl-morpholine; (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexaflu; orophosphate In dichloromethane at 20℃;	98%

: phenyl (3S)-3-amino-4-phenylbut-1-enyl sulfone hydrochloride

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: phenyl (3S)-3-(N-carbobenzyloxyvalyl)amino-4-phenylbut-1-enyl sulfone

Conditions

Conditions	Yield
With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -15 - 20℃;	98%

N-Carbobenzyloxy-L-valine Chemical Properties

Molecular Structure of N-Carbobenzyloxy-L-valine (CAS NO.1149-26-4):

IUPAC Name: 3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid
Empirical Formula: C₁₃H₁₇NO₄
Molecular Weight: 251.2784
H bond acceptors: 5
H bond donors: 2
Freely Rotating Bonds: 6
Index of Refraction: 1.531
Molar Refractivity: 65.81 cm³
Molar Volume: 212.4 cm³
Surface Tension: 45.5 dyne/cm
Density: 1.182 g/cm³
Flash Point: 215.4 °C
Enthalpy of Vaporization: 72.56 kJ/mol
Boiling Point: 432.6 °C at 760 mmHg
Vapour Pressure: 2.99E-08 mmHg at 25°C
Melting point: 62-64 °C(lit.)
Storage temp: 2-8°C
InChI
InChI=1/C13H17NO4/c1-9(2)11(12(15)16)14-13(17)18-8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3,(H,14,17)(H,15,16)
Smiles
C(N[C@@H](C(=O)O)C(C)C)(=O)OCc1ccccc1
EINECS: 214-562-1
Product Categories: Miscellaneous Biochemicals; chiral; protected amino acid & peptides; Valine [Val, V];Z-Amino Acids and Derivatives; Amino Acids; Amino Acids (N-Protected); Biochemistry; Cbz-Amino Acids; Chiral Compounds; Cbz-Amino acid series

N-Carbobenzyloxy-L-valine Safety Profile

N-Carbobenzyloxy-L-valine (CAS NO.1149-26-4)'s Hazard Codes: Irritant Xi, Harmful Xn
N-Carbobenzyloxy-L-valine (CAS NO.1149-26-4)'s Risk Statements:
38: Irritating to the skin
43: May cause sensitization by skin contact
20/21/22: Harmful by inhalation, in contact with skin and if swallowed 36/37/38: Irritating to eyes, respiratory system and skin
N-Carbobenzyloxy-L-valine (CAS NO.1149-26-4)'s Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
36/37: Wear suitable protective clothing and gloves
WGK Germany: 3
Hazard Note: Irritant

N-Carbobenzyloxy-L-valine Specification

N-Carbobenzyloxy-L-valine , with CAS number of 1149-26-4, can be called (2S)-2-{[(Benzyloxy)carbonyl]amino}-3-methylbutanoic acid ; Benzyloxycarbonyl-L-valine ; Carbobenzoxy-L-valine ; DL-Valine, N-[(phenylmethoxy)carbonyl]- ; L-valine, N-[(phenylmethoxy)carbonyl]- ; N-[(Benzyloxy)carbonyl]-L-valin ; N-[(Benzyloxy)carbonyl]-L-valine ; N-Benzyloxycarbonyl-(S)-valine ; N-Carbobenzoxy-DL-valine . It is a white to light yellow crystal powde, N-Carbobenzyloxy-L-valine (CAS NO.1149-26-4) is used as drug intermediates.

Product Name

N-Carbobenzyloxy-L-valine

Synthetic route

N-Carbobenzyloxy-L-valine Chemical Properties

N-Carbobenzyloxy-L-valine Safety Profile

N-Carbobenzyloxy-L-valine Specification

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