tert-butyl (2S)-2-[(2S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxo-propyl]morpholine-4-carboxylate
[CAS# 2641824-60-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: tert-butyl (2S)-2-[(2S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxo-propyl]morpholine-4-carboxylate
• Synonyms: 2-Methyl-2-propanyl (2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methoxy-3-oxopropyl]-4-morpholinecarboxylate
• Molecular Formula: C₂₁H₃₀N₂O₇
• Molecular Weight: 422.47
• CAS Registry Number: 2641824-60-2
• SMILES: CC(C)(C)OC(=O)N1CCO[C@H](C1)C[C@@H](C(=O)OC)NC(=O)OCC2=CC=CC=C2

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 556.9±50.0 °C 760 mmHg (Calc.)^*
• Flash point: 290.6±30.1 °C (Calc.)^*
• Index of refraction: 1.518 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+351+338-P302+352

Discovery and Applications

Tert-butyl (2S)-2-[(2S)-2-(benzyloxycarbonylamino)-3-methoxy-3-oxo-propyl]morpholine-4-carboxylate is a chiral, protected amino acid derivative used as a building block in peptide and peptidomimetic synthesis. The molecule contains a morpholine ring substituted at the 2-position with a side chain bearing a (2S)-configured amino acid unit protected with a benzyloxycarbonyl (Cbz) group and a methoxy ketone functionality. The morpholine nitrogen is substituted with a tert-butyl ester, providing protection of the carboxyl group and enabling selective deprotection in multi-step synthetic sequences. The defined stereochemistry at both the morpholine 2-position and the amino acid α-carbon ensures proper three-dimensional orientation when incorporated into larger molecules.

This intermediate is typically employed in convergent peptide synthesis or as a fragment for assembling peptidomimetic structures. The benzyloxycarbonyl group protects the amine during coupling reactions, while the tert-butyl ester masks the carboxyl functionality, allowing selective deprotection and further coupling to other amino acids or heterocyclic fragments. The methoxy ketone on the side chain can serve as a handle for additional derivatization, including reductive transformations or nucleophilic addition reactions, providing flexibility in the design of functionalized analogues.

Handling of this compound requires standard precautions for chiral and protected intermediates. It is generally supplied as a solid with high purity, and care must be taken to avoid conditions that could remove protecting groups prematurely or racemize the stereocenters. Analytical techniques such as chiral HPLC, NMR, and mass spectrometry are used to confirm stereochemical integrity and purity, ensuring reproducibility in downstream synthetic applications.