benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate

Product Name: benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate
CAS No.: 1194550-59-8
Chemical Name: benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate
Synonyms: (S)-benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride;3-(Methylsulfonyl)-L-phenylalanine phenylmethyl ester hydrochloride;(S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate;(S)-benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate;benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride;Lifitegrast Intermediate 4;Lifitegrast Impurity 11 HCl;(S)-benzyl 2-amino-3-(3-(methyl;Benzyl 3-(methylsulfonyl)-L-phenylalanine hydrochloride;(S)-3-methylsulphonyl-phenylalanine benzylester HCl salt
CBNumber: CB52737329
Molecular Formula: C17H20ClNO4S
Formula Weight: 369.86
MOL File: 1194550-59-8.mol

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benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate Property

storage temp.: Inert atmosphere,Room Temperature
form: Solid
color: White to off-white
InChI: InChI=1/C17H19NO4S.ClH/c1-23(20,21)15-9-5-8-14(10-15)11-16(18)17(19)22-12-13-6-3-2-4-7-13;/h2-10,16H,11-12,18H2,1H3;1H/t16-;/s3
InChIKey: QMFDSGLDMSBMLX-LSQUZMQTNA-N
SMILES: C(C1C=CC=C(S(=O)(=O)C)C=1)[C@H](N)C(=O)OCC1C=CC=CC=1.Cl |&1:11,r|

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Safety

HS Code: 2921199990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: B285425
Product name: (S)-Benzyl2-Amino-3-(3-(methylsulfonyl)phenyl)propanoateHydrochloride
Packaging: 500mg
Price: $110
Updated: 2021/12/16

Activate Scientific

Product number: AS49492
Product name: (S)-Benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride
Purity: 97% ee
Packaging: 1g
Price: $86
Updated: 2021/12/16

Activate Scientific

Product number: AS49492
Product name: (S)-Benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride
Purity: 97% ee
Packaging: 5G
Price: $302
Updated: 2021/12/16

AK Scientific

Product number: 3356DF
Product name: (S)-Benzyl2-amino-3-(3-(methylsulfonyl)phenyl)propanoatehydrochloride
Packaging: 5g
Price: $303
Updated: 2021/12/16

BLDpharm

Product number: BD317776
Product name: (S)-Benzyl2-amino-3-(3-(methylsulfonyl)phenyl)propanoatehydrochloride
Purity: 97%
Packaging: 1g
Price: $43
Updated: 2021/12/16

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benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate Chemical Properties,Usage,Production

Uses

(S)-Benzyl 2-Amino-3-(3-(methylsulfonyl)phenyl)propanoate Hydrochloride is a reagent in the development of potent LFA-1/ICAM antagonist SAR 118 as an opthalmic solution for treating dry eyes. Preparation of crystalline isoquinoline derivative as LFA-1 inhibitors.

Synthesis

1289646-78-1

1194550-59-8

The general procedure for the synthesis of benzyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride from benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate is as follows: firstly, using sodium bicarbonate (3 eq.) and tert-butyl dicarbonate (Boc2O, 1.1 eq.) in a solvent mixture of dioxane and water. tert-butoxycarbonyl (Boc) protection of the amino group of bromophenylalanine, and the reaction afforded compound 7 in 98% yield.Subsequently, the reaction was carried out by cuprous iodide (0.4 eq.), cesium carbonate (0.5 eq.), L-proline (0.8 eq.), and the sodium salt of methanesulfinic acid (3.9 eq.) in dimethylsulfoxide (DMSO) for 9 hr. at 95-100 °C, during which two Additional addition of cuprous iodide (0.2 eq.) and L-proline (0.4 eq.) introduced the methanesulfonyl functional group, which was isolated in 96% yield to give compound 8. Next, using benzyl alcohol (1.1 eq.), 4-dimethylaminopyridine (DMAP, 0.1 eq.) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC, 1.0 eq. ), the carboxylic acid group of compound 8 was converted to a benzyl ester to give compound 9 in 99% yield. Finally, the deprotection reaction of the amino group was carried out by adding a dioxane solution of 4N HCl to a dichloromethane solution of compound 9 at 0 °C to isolate the hydrochloride salt of the free amino group, compound 10, in 94% yield.

References

[1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 3, p. 203 - 206
[2] Patent: WO2014/18748, 2014, A1. Location in patent: Paragraph 00120; 00121; 00122; 00123; 00124; 001

benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate Preparation Products And Raw materials

Raw materials

Preparation Products

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benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate Suppliers

Canada 1 China 130 India 4 United States 4 Global 139

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View Lastest Price from benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate manufacturers

Henan Aochuang Chemical Co.,Ltd.

Product: benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate 1194550-59-8
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-09-30

Career Henan Chemical Co

Product: 3-(Methylsulfonyl)-L-phenylalanine phenylmethyl ester hydrochloride 1194550-59-8
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 100KG
Release date: 2018-12-25

1194550-59-8, benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoateRelated Search:

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benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate

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benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride

Lifitegrast Intermediate 4

Benzyl (S)-2-Amino-3-(3-(Methylsulfonyl)Phenyl)Propanoatebenzyl (S)-2-Amino-3-(3-(Methylsulfonyl)Phenyl)Propanoate

(S)-benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate

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(S)-Benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride(For export only)

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benzyl (2S)-2-amino-3-(3-methanesulfonylphenyl)propanoate hydrochloride

Benzyl 3-(methylsulfonyl)-L-phenylalanine hydrochloride

L-Phenylalanine, 3-(methylsulfonyl)-,phenylmethyl ester .HCl

Lifitegrast Impurity 11 HCl

(S)-3-methylsulphonyl-phenylalanine benzylester HCl salt

1194550-59-8

C17H19NO4SClH

C17H19NO4SHCl

1194550-59-8