3-(Benzyloxy)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate

Base Information

• Chemical Name: 3-(Benzyloxy)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate
• CAS No.: 47173-80-8
• Molecular Formula: C15H21NO5
• Molecular Weight: 295.335
• Hs Code.: 2924 29 70
• DSSTox Substance ID: DTXSID80963760
• Wikidata: Q72448677
• Mol file: 47173-80-8.mol

Synonyms:DTXSID80963760;3-(Benzyloxy)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate

Chemical Property of 3-(Benzyloxy)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 4.07E-09mmHg at 25°C
• Melting Point: 58-60 °C(lit.)
• Refractive Index: -20 ° (C=2, 80% EtOH)
• Boiling Point: 456.2 °C at 760 mmHg
• PKA: 3.53±0.10(Predicted)
• Flash Point: 229.7 °C
• PSA: 84.86000
• Density: 1.174 g/cm³
• LogP: 2.57200
• Storage Temp.: 2-8°C
• Solubility.: almost transparency in Methanol
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 294.13414774
• Heavy Atom Count: 21
• Complexity: 339

Purity/Quality:

99% ^*data from raw suppliers

Boc-O-benzyl-D-serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(COCC1=CC=CC=C1)C(=O)[O-]
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](COCC1=CC=CC=C1)C(=O)[O-]
• Uses: N-BOC-O-Benzyl-D-serine, is an amino acid derivative used in chemical synthesis and peptide chemistry.is used in preparation of substituted naphthyl thiadiazolidinones as protein tyrosine phosphatase degraders for treating cancer and metabolic diseases.

Technology Process of 3-(Benzyloxy)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate

There total 8 articles about 3-(Benzyloxy)-2-{[tert-butoxy(hydroxy)methylidene]amino}propanoate 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: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + O-benzyl-D-serine (10433-52-0,32520-12-0) → N-Boc-D-serine(Bzl)-OH (47173-80-8)

Guidance literature:

In tetrahydrofuran; water;

DOI:10.1080/07328319708006220

Reference yield: 75.0%

(R)-N-tert-butoxycarbonyl serine (3262-72-4,3850-40-6,6368-20-3,90582-28-8,84311-18-2) + benzyl bromide (100-39-0) → N-Boc-D-serine(Bzl)-OH (47173-80-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -40 ℃; for 5h;

DOI:10.1016/j.cclet.2012.03.032

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + O-benzylserine (5445-44-3,32520-12-0) → O-benzyl-N-(tert-butoxycarbonyl)serine (23680-31-1,47173-80-8,94347-12-3,53317-22-9)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 0 - 20 ℃;

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

O-benzylserine

N-Boc-DL-serine

di-tert-butyl dicarbonate

Downstream raw materials:

3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid vinyl ester

C₂₈H₃₄N₂O₅

C₂₈H₃₇N₃O₆S

C₂₈H₃₇N₃O₆S

Refernces

• 1、 Qi, Xian Liang,Yang, Er Qun,Zhang, Jun Tao,Wang, Tao,Cao, Xiao Ping. "A facile synthesis of the spiroindoline-based growth hormone secretagogue, MK-677". scheme or table. p. 661 - 664. Retrieved 2012/07/03.
• 2、 -. "GROWTH HORMONE SECRETAGOGUES". Page/Page column 109. . Retrieved 2010/02/07.