(S)-(+)-2-Hydroxy-4-phthalimidobutyric Acid

Base Information

• Chemical Name: (S)-(+)-2-Hydroxy-4-phthalimidobutyric Acid
• CAS No.: 48172-10-7
• Molecular Formula: C12H11NO5
• Molecular Weight: 249.223
• Hs Code.: 2925190090
• European Community (EC) Number: 624-172-7
• DSSTox Substance ID: DTXSID00350835
• Nikkaji Number: J991.400E
• Wikidata: Q72472824
• Mol file: 48172-10-7.mol

Synonyms:48172-10-7;(S)-(+)-2-Hydroxy-4-phthalimidobutyric Acid;(S)-4-(1,3-Dioxoisoindolin-2-yl)-2-hydroxybutanoic acid;(2S)-4-(1,3-Dioxoisoindolin-2-yl)-2-hydroxybutanoic acid;(2S)-4-(1,3-dioxoisoindol-2-yl)-2-hydroxybutanoic acid;(S)-(+)-alpha-Hydroxy-1,3-dioxo-2-isoindolinebutyric acid;SCHEMBL1781793;(S)-(+)-a-Hydroxy-1,3-dioxo-2-isoindolinebutyric acid;DTXSID00350835;MFCD00192213;AKOS015855367;AKOS016005508;AS-10800;BP-12906;CS-0312138;H0933;S-4-Phthalimido-2-hydroxy butyric acid(PHBA);T72512;(S)-(+)- alpha -Hydroxy-1,3-dioxo-2-isoindolinebutyric acid;(S)-(+)-alpha-Hydroxy-1,3-dioxo-2-isoindolinebutyric acid, 98%;(2S)-4-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxybutanoic acid

Chemical Property of (S)-(+)-2-Hydroxy-4-phthalimidobutyric Acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.37E-11mmHg at 25°C
• Melting Point: 157-159 °C(lit.)
• Refractive Index: 6 ° (C=1, MeOH)
• Boiling Point: 513.1 °C at 760 mmHg
• PKA: 3.67±0.10(Predicted)
• Flash Point: 264.1 °C
• PSA: 94.91000
• Density: 1.504 g/cm³
• LogP: 0.05610
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: almost transparency in Methanol
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 249.06372245
• Heavy Atom Count: 18
• Complexity: 357

Purity/Quality:

99% ^*data from raw suppliers

(S)-(+)-2-Hydroxy-4-phthalimidobutyric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CCC(C(=O)O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CC[C@@H](C(=O)O)O
• Uses: (S)-(+)-2-Hydroxy-4-phthalimidobutyric Acid is used in preparation method of plazomicin key intermediate for simplifying operation and improving yield.

Technology Process of (S)-(+)-2-Hydroxy-4-phthalimidobutyric Acid

There total 2 articles about (S)-(+)-2-Hydroxy-4-phthalimidobutyric Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

phthalic anhydride (85-44-9) + L-γ-hydroxylamino-α-hydroxybutyric acid → (+)-(2S)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxybutanoic acid (48172-10-7,31701-91-4)

Guidance literature:

In cyclohexane; at 90 - 110 ℃; for 5.66h; under 12.7513 Torr;

Reference yield:

phthalic anhydride (85-44-9) + (S)-4-amino-2-hydroxybutanoic acid (3938-83-8,13477-53-7,31771-40-1,40371-51-5) → (+)-(2S)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxybutanoic acid (48172-10-7,31701-91-4)

Guidance literature:

at 140 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2009.03.072

Reference yield: 73.7%

(+)-(2S)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxybutanoic acid (48172-10-7,31701-91-4) + kanamycin A → amikacin

Guidance literature:

kanamycin A; In acetonitrile; for 0.166667h;

With 1,1,1,3,3,3-hexamethyl-disilazane; at 75 - 80 ℃; for 8h;

(+)-(2S)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxybutanoic acid; Concentration; Further stages;

upstream raw materials:

phthalic anhydride

(S)-4-amino-2-hydroxybutanoic acid

Downstream raw materials:

(S)-benzyl 4-(1,3-dioxoisoindolin-2-yl)-2-hydroxybutanoate

Refernces

• 1、 -. "A method for improving the yield of the method of preparing the amikacin". Paragraph 0004; 0005; 0053; 0054. . Retrieved 2017/07/14.