2,5-Oxazolidinedione,4-(phenylmethyl)-, (4S)- supplier

Name
(S)-(-)-4-BENZYLOXAZOLIDINE-2,5-DIONE
EINECS
CAS No. 14825-82-2
Article Data47
CAS DataBase
Density 1.3 g/cm³
Solubility
Melting Point 90 °C
Formula C₁₀H₉NO₃
Boiling Point
Molecular Weight 191.186
Flash Point
Transport Information
Appearance
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,5-Oxazolidinedione,4-(phenylmethyl)-, (S)-;2,5-Oxazolidinedione, 4-benzyl-, L- (8CI);(-)-4-Benzyl-2,5-oxazolidinedione;(S)-4-(Phenylmethyl)-2,5-oxazolidinedione;L-Phenylalanine N-carboxy anhydride;N-Carboxy-L-phenylalanine anhydride;N-Carboxy-L-phenylalanine cyclic anhydride;Phenylalanine N-carboxy anhydride;Phenylalanine-N-carboxy acid anhydride;(4S)-4-Benzyl-1,3-oxazolidine-2,5-dione;
PSA 55.40000
LogP 1.19290

Synthetic route

: 79-37-8
oxalyl dichloride

: 130529-77-0
C20H33NO4Si

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;	100%

: 32315-10-9
bis(trichloromethyl) carbonate

: 16480-57-2
L-phenylalanine sodium salt

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
With 4-methyl-morpholine In water; acetonitrile at 20℃; for 0.00277778h; Reagent/catalyst; Flow reactor; Inert atmosphere;	100%
Stage #1: bis(trichloromethyl) carbonate; L-phenylalanine sodium salt With 4-methyl-morpholine In water; acetonitrile at 20℃; for 2.77778E-05h; Stage #2: In water; ethyl acetate; acetonitrile at 20℃; for 0.000261111h; Solvent; Reagent/catalyst;	100%

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
With phosphorus trichloride In dichloromethane at 0℃; for 2h;	98%
With bis(trichloromethyl) carbonate; triethylamine In ethyl acetate Ambient temperature;	75%

: 32315-10-9
bis(trichloromethyl) carbonate

: 63-91-2
L-phenylalanine

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃;	94%
In tetrahydrofuran at 40℃; Inert atmosphere;	91.5%
In tetrahydrofuran at 50℃; Inert atmosphere;	84%

: 116-16-5
1,1,1,3,3,3-hexachloro-propan-2-one

: 63-91-2
L-phenylalanine

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃; Inert atmosphere;	91.5%

: 75-44-5
phosgene

: 63-91-2
L-phenylalanine

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
In tetrahydrofuran; toluene at 50℃; for 1h;	86%
In tetrahydrofuran; toluene at 50℃; for 1.5h;	86%

: 63-91-2
L-phenylalanine

: 503-38-8
trichloromethyl chloroformate

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
With pyrographite In tetrahydrofuran at 55℃; for 0.5h;	86%
In tetrahydrofuran at 40 - 50℃; for 3h;	42.8%
In tetrahydrofuran phosgenation;

: N-phenoxycarbonyl-L-phenylalanine

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
Stage #1: N-phenoxycarbonyl-L-phenylalanine With acetic acid In acetonitrile at 80℃; Inert atmosphere; Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; for 1h; Inert atmosphere;	78%

: 1161-13-3
N-Cbz-L-Phe

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
With 1-pyrrolidinecarboxaldehyde; 1,3,5-trichloro-2,4,6-triazine In acetonitrile at 20℃; for 8h;	69%

: 41844-91-1
N-methoxycarbonyl-L-phenylalanine

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
With phosphorus tribromide In diethyl ether	66.8%

: 67-66-3
chloroform

: 63-91-2
L-phenylalanine

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
With 4-methyl-morpholine; oxygen at 60℃; Reagent/catalyst; UV-irradiation;	62%
With oxygen In acetonitrile at 70℃; Temperature; UV-irradiation;

: 24424-95-1
di-tert-butyl tricarbonate

: 63-91-2
L-phenylalanine

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
In tetrahydrofuran at 60℃; for 4h;	25%

: 32315-10-9
bis(trichloromethyl) carbonate

: 17585-69-2, 27172-85-6, 28069-46-7, 74496-49-4, 79541-99-4
L-phenylalanine hydrochloride

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
With TEA In tetrahydrofuran at 55 - 60℃;

: 63-91-2
L-phenylalanine

(CCl3O)2CO: (CCl3O)2CO

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
In tetrahydrofuran at 55℃; for 2h;

: 949-45-1
(S)-3-phenyl-2-ureido-propionic acid

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
With oxygen; nitrogen(II) oxide

: 63-91-2
L-phenylalanine

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / aq. NaOH 2: 66.8 percent / PBr3 / diethyl ether View Scheme

: 52641-32-4
N-benzyloxycarbonyl-L-phenylalanyl chloride

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

Conditions

Conditions	Yield
In tetrahydrofuran; hexane at 40℃; for 12h;

: 75-31-0
isopropylamine

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: 278185-22-1
(S)-2-amino-N-isopropyl-3-phenylpropanamide

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.0125h; Flow reactor;	91%
In dichloromethane at 20℃; for 0.00277778h;

: 4101-30-8
2-amino-4,5-dimethoxyacetophenone

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: (S)-3-benzyl-7,8-dimethoxy-5-methyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions

Conditions	Yield
Stage #1: 2-amino-4,5-dimethoxyacetophenone; L-phenylalanine-N-carboxyanhydride With trifluoroacetic acid In toluene at 60℃; for 0.5h; Sealed tube; Stage #2: With triethylamine at 80℃; for 0.5h; Sealed tube;	90%

: 2835-77-0
(2-aminophenyl)(phenyl)methanone

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: 884492-66-4
(S)-3-benzyl-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions

Conditions	Yield
Stage #1: (2-aminophenyl)(phenyl)methanone; L-phenylalanine-N-carboxyanhydride With trifluoroacetic acid In toluene at 60℃; for 0.5h; Sealed tube; Stage #2: With triethylamine at 80℃; for 0.5h; Sealed tube;	88%

iBu(Z-Lys)30: iBu(Z-Lys)30

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

iBu(Z-Lys)30-b-(Phe)15: iBu(Z-Lys)30-b-(Phe)15

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 24h;	85%

: 719-59-5
2-Amino-5-chlorobenzophenone

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: 39200-49-2
(S)-3-benzyl-7-chloro-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions

Conditions	Yield
Stage #1: 5-chloro-2-aminobenzophenone; L-phenylalanine-N-carboxyanhydride With trifluoroacetic acid In toluene at 60℃; for 0.5h; Sealed tube; Stage #2: With triethylamine at 80℃; for 0.5h; Sealed tube;	83%

: 551-93-9
2-aminoacetophenone

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: (S)-3-benzyl-5-methyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions

Conditions	Yield
Stage #1: 2-aminoacetophenone; L-phenylalanine-N-carboxyanhydride With trifluoroacetic acid In toluene at 60℃; for 0.5h; Sealed tube; Stage #2: With triethylamine at 80℃; for 0.5h; Sealed tube;	82%

: 133776-50-8
4-(2-aminobenzoyl)benzonitrile

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: (S)-4-(3-benzyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)benzonitrile

Conditions

Conditions	Yield
Stage #1: 4-(2-aminobenzoyl)benzonitrile; L-phenylalanine-N-carboxyanhydride With trifluoroacetic acid In toluene at 60℃; for 0.5h; Sealed tube; Stage #2: With triethylamine at 80℃; for 0.5h; Sealed tube;	82%

: 4651-72-3
2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: (S)-3-benzyl-5-phenyl-1,3,6,7,8,9-hexahydro-2H-benzo[4,5]thieno[2,3-e][1,4]diazepin-2-one

Conditions

Conditions	Yield
Stage #1: 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene; L-phenylalanine-N-carboxyanhydride With trifluoroacetic acid In toluene at 60℃; for 0.5h; Sealed tube; Stage #2: With triethylamine at 80℃; for 0.5h; Sealed tube;	82%

: 39859-36-4
2-amino-5-bromobenzophenone

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: (S)-3-benzyl-7-bromo-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions

Conditions	Yield
Stage #1: 2-amino-5-bromobenzophenone; L-phenylalanine-N-carboxyanhydride With trifluoroacetic acid In toluene at 60℃; for 0.5h; Sealed tube; Stage #2: With triethylamine at 80℃; for 0.5h; Sealed tube;	79%

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: 2633-66-1
2-mesitylmagnesium bromide

: 79137-56-7
(S)-3-phenyl-2-(2,4,6-trimethylbenzamido)propanoic acid

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78 - 20℃; for 1.33h; Inert atmosphere;	75%

: 784-38-3
2-amino-5-chloro-2'-fluorobenzophenone

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: (S)-3-benzyl-7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions

Conditions	Yield
Stage #1: 2-amino-5-chloro-2'-fluorobenzophenone; L-phenylalanine-N-carboxyanhydride With trifluoroacetic acid In toluene at 60℃; for 0.5h; Sealed tube; Stage #2: With triethylamine at 80℃; for 0.5h; Sealed tube;	74%

: 49615-96-5
1-(3-aminobenzofuran-2-yl)ethan-1-one

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: (S)-3-benzyl-5-methyl-1,3-dihydro-2H-benzofuro[3,2-e][1,4]diazepin-2-one

Conditions

Conditions	Yield
Stage #1: 1-(3-aminobenzofuran-2-yl)ethan-1-one; L-phenylalanine-N-carboxyanhydride With trifluoroacetic acid In toluene at 60℃; for 0.5h; Sealed tube; Stage #2: With triethylamine at 80℃; for 0.5h; Sealed tube;	68%

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: 1-phenylalanine-1-deutero-2-phenylethylamide

Conditions

Conditions	Yield
Stage #1: L-phenylalanine-N-carboxyanhydride With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In tetrahydrofuran; diethyl ether for 24h; complexation; Stage #2: With diclazuril In tetrahydrofuran; water-d2 acidolysis; Further stages.;	63%

: 79-22-1
methyl chloroformate

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

A: 2-Aminoindanone hydrochloride

B: (R)-2-p-Toluoylpyrrolidine hydrochloride

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane for 4h; Yields of byproduct given. Title compound not separated from byproducts;	A 25% B n/a

...Expand

: 90-46-0
9-hydroxyxanthene

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: 108276-19-3
(S)-4-benzyl-3-xanthen-9-yl-oxazolidine-2,5-dione

Conditions

Conditions	Yield
In toluene Heating;

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: 127-06-0
acetone oxime

: C12H16N2O2

Conditions

Conditions	Yield
With hydrogenchloride

: 613-91-2
acetophenone oxime

: 14825-82-2
L-phenylalanine-N-carboxyanhydride

: C17H18N2O2

Conditions

Conditions	Yield
With hydrogenchloride

2,5-Oxazolidinedione,4-(phenylmethyl)-, (4S)- Specification

The 2,5-Oxazolidinedione,4-(phenylmethyl)-, (4S)-, with the CAS registry number 14825-82-2, is also known as L-Phenylalanine N-carboxy anhydride. This chemical's molecular formula is C₁₀H₉NO₃ and molecular weight is 191.18. What's more, its systematic name is (4S)-4-benzyl-1,3-oxazolidine-2,5-dione. You should not breathe dust. When using it, you must avoid contact with skin and eyes.

Physical properties of 2,5-Oxazolidinedione,4-(phenylmethyl)-, (4S)- are: (1)ACD/LogP: 1.28; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1; (4)ACD/LogD (pH 7.4): 1; (5)ACD/BCF (pH 5.5): 6; (6)ACD/BCF (pH 7.4): 6; (7)ACD/KOC (pH 5.5): 121; (8)ACD/KOC (pH 7.4): 120; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 55.4 Å²; (13)Index of Refraction: 1.569; (14)Molar Refractivity: 48.216 cm³; (15)Molar Volume: 147.089 cm³; (16)Polarizability: 19.114×10^-24cm³; (17)Surface Tension: 50.081 dyne/cm; (18)Density: 1.3 g/cm³.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2N[C@@H](Cc1ccccc1)C(=O)O2
(2)InChI: InChI=1S/C10H9NO3/c12-9-8(11-10(13)14-9)6-7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,13)/t8-/m0/s1
(3)InChIKey: GQBIVYSGPXCELZ-QMMMGPOBSA-N

Product Name

(S)-(-)-4-BENZYLOXAZOLIDINE-2,5-DIONE

Synthetic route

2,5-Oxazolidinedione,4-(phenylmethyl)-, (4S)- Specification

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