N-BOC-O-Benzyl-L-serine CAS 23680-31-1

Introduction：Basic information about N-BOC-O-Benzyl-L-serine CAS 23680-31-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

N-BOC-O-Benzyl-L-serine Basic information

• Product Name: N-BOC-O-Benzyl-L-serine
• Synonyms: N-BOC-O-Benzyl-L-ser;N-Boc-O-benzyl-L-serineBoc-Ser(Bzl)-OH;Boc-Ser(Bz1)-OH;(S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)aMino)propanoic acid;N-BOC-O-BENZYL-SERINE;(2S)-3-Benzyloxy-2-(tert-butoxycarbonylamino)propanoic acid;L-SERINE-N-T-BOC, O-BZ ETHER (15N);L-SERINE-N-T-BOC, O-BZ ETHER (2-13C)
• CAS: 23680-31-1
• MF: C15H21NO5
• MW: 295.33
• EINECS: 245-820-1
• Product Categories: Boc-Amino Acids;Boc-Amino acid series;Boc-Amino Acids and Derivative;Amino Acids;Amino Acids (N-Protected);Biochemistry
• Mol File: 23680-31-1.mol

N-BOC-O-Benzyl-L-serine Chemical Properties

• Melting point: 58-60 °C(lit.)
• alpha: 21.5 º (c=2, ethanol)
• Boiling point: 437.02°C (rough estimate)
• density: 1.1454 (rough estimate)
• refractive index: 22 ° (C=2, EtOH)
• storage temp.: Keep in dark place,Sealed in dry,Room Temperature
• solubility: Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
• pka: 3.53±0.10(Predicted)
• form: Solid
• color: White to Almost white
• Optical Rotation: [α]20/D +20±1°, c = 2% in ethanol: water (4:1)
• BRN: 3064461
• Major Application: peptide synthesis
• InChI: 1S/C15H21NO5/c1-15(2,3)21-14(19)16-12(13(17)18)10-20-9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,16,19)(H,17,18)/t12-/m0/s1
• InChIKey: DMBKPDOAQVGTST-LBPRGKRZSA-N
• SMILES: CC(C)(C)OC(=O)N[C@@H](COCc1ccccc1)C(O)=O
• CAS DataBase Reference: 23680-31-1(CAS DataBase Reference)
• EPA Substance Registry System: N-tert-Butoxycarbonyl-O-benzyl-L-serine (23680-31-1)

Safety Information

• Hazard Codes: Xn
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• TSCA: TSCA listed
• HS Code: 2924 29 70
• HazardClass: IRRITANT
• Storage Class: 11 - Combustible Solids

N-BOC-O-Benzyl-L-serine Usage And Synthesis

Chemical Properties

White powder

Uses

N-Boc-O-benzyl-L-serine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

3262-72-4

100-39-0

23680-31-1

Example 36 Synthesis of N-tert-butoxycarbonyl-O-benzyl-L-serine 39: Boc-L-serine (15 g, 73.09 mmol) was dissolved in DMF (300 mL) at 0 °C, NaH (6.43 g, 160.80 mmol, 60% mineral oil dispersion) was slowly added, and the reaction temperature was maintained at 0 °C and stirred for 1.5 hours. Subsequently, benzyl bromide (13.75 g, 80.40 mmol) was added, and the reaction mixture was gradually warmed to room temperature and continued to stir overnight. Upon completion of the reaction, DMF was removed by evaporation under reduced pressure and the residue was dissolved in H2O. The crude product was partitioned between water and Et2O. The aqueous phase was acidified with 3N HCl to pH < 4 and then extracted three times with EtOAc. The EtOAc extracts were combined, washed with H2O, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give N-tert-butoxycarbonyl-O-benzyl-L-serine (17.27 g, 80% yield).

References

[1] Tetrahedron Letters, 2012, vol. 53, # 26, p. 3225 - 3229
[2] Patent: US2004/121316, 2004, A1
[3] Patent: US2005/239054, 2005, A1
[4] Patent: WO2014/120783, 2014, A1. Location in patent: Paragraph 00145
[5] Patent: WO2018/26763, 2018, A1. Location in patent: Page/Page column 81

N-BOC-O-Benzyl-L-serine Preparation Products And Raw materials

• Raw materials: Hydrochloric acid-->Ethyl acetate-->Diethyl ether-->N,N-Dimethylformamide-->Sodium hydride-->1,4-Dioxane-->Benzyl bromide-->BOC-L-Serine-->O-BENZYL-L-SERINE-->Mineral oil
• Preparation Products: Alanine, 3-(benzyloxy)-N-carboxy-, di-tert-butyl ester (7CI)-->L-SERINE(BENZYL ETHER) ETHYL ESTER HCL-->BOC-O-BENZYL-L-SERINE N,O-DIMETHYLHYDROXAMIDE