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N-Carbobenzyloxy-L-valine
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Name

N-Carbobenzyloxy-L-valine

 EINECS 214-562-1
CAS No. 1149-26-4 Density 1.182 g/cm3
PSA 75.63000 LogP 2.41290
Solubility N/A 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 N/A Appearance white to light yellow crystal powder
Safety 36/37-36-26 Risk Codes 38-43-36/37/38-20/21/22
Molecular Structure Molecular Structure of 1149-26-4 (N-Carbobenzyloxy-L-valine) Hazard Symbols IrritantXi,HarmfulXn
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;

Article Data 91

N-Carbobenzyloxy-L-valine Synthetic route

72-18-4

L-valine

501-53-1

benzyl chloroformate

1149-26-4

(S)-N-(benzyloxycarbonyl)valine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
Stage #1: DL-Val/PyS With alpha cyclodextrin In ethanol; dimethyl sulfoxide at 30℃; for 24h;
Stage #2: benzyl chloroformate
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 16h; Solvent; Temperature;

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: IrritantXi,HarmfulXn
 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.

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