IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data
Identification
Product NameH-Glu-OtBuIUPAC Name(4S)-4-amino-5--5-oxopentanoic acid Molecular StructureCAS Registry Number 45120-30-7MDL NumberMFCD00038562Synonyms45120-30-7h-glu-otbu(S)-4-Amino-5-(tert-butoxy)-5-oxopentanoic acid1-tert-Butyl L-glutamate25456-75-1L-Glutamic acid a-tert-butyl esterL-Glutamic acid alpha-tert-butyl ester(4S)-4-amino-5--5-oxopentanoic acidL-Glutamic acid 1-tert-butyl ester(4S)-4-azaniumyl-5--5-oxopentanoateL-Glu-OtBuEINECS 247-005-6MFCD00038562Glu-OtBuH-GluOtBua-tert-Butyl L-glutamateL-Glutamic acid |A-tert inverted exclamation mark currencybutyl esterglutamic acid t-butyl esterSCHEMBL337707DTXSID40963342L-Glutamic acid |A-tert.butyl esterAKOS015995186AM81742CS-W018940FD21402HY-W018154AC-32536AS-103971-(1,1-Dimethylethyl) hydrogen L-glutamateB3000L-Glutamicacid, 1-(1,1-dimethylethyl) esterEN300-260313(4s)-4-amino-5-tert-butoxy-5-oxopentanoic acid(S)-4-amino-5-tert-butoxy-5-oxopentanoic acid(S)-2-aminopentanedioic acid 1-tert.-butyl esterA872423J-505143(4S)-4-AMINO-5-(TERT-BUTOXY)-5-OXOPENTANOIC ACIDMolecular FormulaC9H17NO4Molecular Weight203.24InChI InChI=1S/C9H17NO4/c1-9(2,3)14-8(13)6(10)4-5-7(11)12/h6H,4-5,10H2,1-3H3,(H,11,12)/t6-/m0/s1 InChI KeyQVAQMUAKTNUNLN-LURJTMIESA-N Isomeric SMILESQVAQMUAKTNUNLN-LURJTMIESA-N
Physical Data
AppearanceWhite powder
Melting Point, °C 147 - 148143 - 144
Spectra
H-Glu-OtBu CAS#: 45120-30-7
Route of Synthesis (ROS)
H-Glu-OtBu CAS 45120-30-7
ConditionsYieldWith N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 30℃; for 3.5h;Experimental Procedure2 Example 2: Synthesis of Palmitoyl-Glu-OtBuWeigh 160g of Palmitoyl-OSu activated ester (0.45mol),Add 1.6L of dichloromethane,138 g of L-glutamic acid-1-tert-butyl ester (0.0.68 mol) was added, and 87.7 g of N,N'-diisopropylethylamine (0.68 mol) was added dropwise thereto, and the reaction was kept at room temperature (20 ° C to 30 ° C). 3.5 hours.The reaction solution was washed twice with 1.6 L of a 10% aqueous potassium hydrogensulfate solution, and the mixture was separated. The organic phase was collected and washed once with 1.6 L of water. The organic phase was concentrated to dryness.Filtration and drying gave 184 g of Palmitoyl-Glu-OtBu, HPLC purity: 98.6%, yield: 93%.93%With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h;Experimental ProcedurePreparation of N-palmitoyl L-glutamic acid a-t-butoxy ester (ABL3)Preparation of N-palmitoyl L-glutamic acid a-t-butoxy ester (ABL3)Palmitic acid ABL1 (1 .0 g, 3.8 mmol) in THF (10 mL) was treated with N-hydroxy succinimide (0.9 g, 7.6 mmol) and diisopropylcarbodiimide (1 .2 mL, 7.6 mmol) overnight to afford ester (ABL2). The precipitate was removed by filtration, and the volatiles were evaporated in vacuo. The resulting residue was dissolved in DMF (6 mL) and treated with glutamic acid t-butyl ester (0.7 g, 3.4 mmol) and DIEA (1 .8 mL, 10 mmol). After 2 h, the reaction mixture was diluted with water, and the desired product was extracted with Et20. The ether layer was dried over Na2S04, concentrated in vacuo, and the crude mass was purified by Si02 chromatography to afford off-white solid ABL3 (1 .2 g, 74% yield). AP-ESI+ Mass calcd C25H47NO5: 441 .3, Found: 464.0 +74%
Safety and Hazards
Pictogram(s)SignalWarningGHS Hazard StatementsH315 (100%): Causes skin irritation H319 (100%): Causes serious eye irritation H335 (100%): May cause respiratory irritation Precautionary Statement CodesP261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501(The corresponding statement to each P-code can be found at the GHS Classification page.)
Other Data
StorageStore at 2~8°, away from light.Shelf Life1 year
DruglikenessLipinski rules componentMolecular Weight203.238logP0.438HBA5HBD2Matching Lipinski Rules4Veber rules componentPolar Surface Area (PSA)89.62Rotatable Bond (RotB)6Matching Veber Rules2
Use PatternH-Glu-OtBu CAS#: 45120-30-7 an intermediate in the synthesis of semaglutide and likely plays a crucial role as an intermediate in the synthesis of semaglutide, contributing to its structural integrity, reactivity, and overall efficiency of production. Its inclusion in the synthesis pathway may offer advantages in terms of stability, purity and synthetic efficiency, ultimately supporting the successful development and manufacture of semaglutide for therapeutic use.
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