Identification | Back Directory | [Name]
benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate | [CAS]
1194550-59-8 | [Synonyms]
Lifitegrast Intermediate 4 (S)-benzyl 2-amino-3-(3-(methyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate benzyl (2S)-2-amino-3-(3-methanesulfonylphenyl)propanoate benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate (S)-benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate 3-(Methylsulfonyl)-L-phenylalanine phenylmethyl ester hydrochloride Benzyl (2S)-2-amino-3-(3-methylsulfonylphenyl)propanoate hydrochloride benzyl (2S)-2-amino-3-(3-methanesulfonylphenyl)propanoate hydrochloride benzyl (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride (S)-benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride 3-(Methylsulfonyl)-L-phenylalanine phenylmethyl ester hydrochloride (1:1) L-Phenylalanine, 3-(methylsulfonyl)-, phenylmethyl ester, hydrochloride (1:1) (S)-Benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride(For export only) Benzyl (S)-2-Amino-3-(3-(Methylsulfonyl)Phenyl)Propanoatebenzyl (S)-2-Amino-3-(3-(Methylsulfonyl)Phenyl)Propanoate | [EINECS(EC#)]
811-561-3 | [Molecular Formula]
C17H19NO4S | [MDL Number]
MFCD29919305 | [MOL File]
1194550-59-8.mol | [Molecular Weight]
333.402 |
Chemical Properties | Back Directory | [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| |
Hazard Information | Back Directory | [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]
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 |
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