(s)-4-(tert-butoxycarbonyl)Morpholine-2-carboxylic acid

Name: (s)-4-(tert-butoxycarbonyl)Morpholine-2-carboxylic acid
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CAS No. 868689-63-8
Cat. No. CS-W019899
Purity≥96%
MDL No.MFCD06200662

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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(s)-4-(tert-butoxycarbonyl)Morpholine-2-carboxylic acid|CS-W019899

Structure of 868689-63-8

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General Information

CAS No. 868689-63-8
Cat. No. CS-W019899
Purity ≥96%
MDL No. MFCD06200662
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₇NO₅
Molecular Weight None
Synonym(s) (S)-N-Boc-2-morpholinecarboxylic acid; (2S)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid
SMILES CC(C)(C)OC(N1C[C@H](OCC1)C(O)=O)=O

Description

This bench-stable, moisture-tolerant building block features a protected morpholine ring with a carboxylic acid handle. The tert-butoxycarbonyl group enables selective deprotection during peptide synthesis, while the electron-rich heterocycle supports diverse coupling reactions under standard conditions.

Application

(S)-4-(tert-Butoxycarbonyl)morpholine-2-carboxylic acid serves as a key chiral building block for the synthesis of morpholine-containing peptidomimetics and bioactive heterocycles. The protected amine and carboxylic acid functionalities enable orthogonal transformations in solid-phase and solution-phase peptide coupling. Its bench-stable tert-butyl carbamate group facilitates selective deprotection under mild acidic conditions, while the morpholine core provides structural rigidity and hydrogen-bonding capacity relevant to drug-like scaffolds.

Synthesis

Route1
- In-stock
  
  135065-76-8
- ~%
- In-stock
  
  868689-63-8
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 18, # 20 p. 5550 - 5553
Route2
- 1030837-49-0
- In-stock
  
  24424-99-5
- ~97%
- In-stock
  
  868689-63-8
References
- Fish, Paul V.; Mackenny, Malcolm; Bish, Gerwyn; Buxton, Timothy; Cave, Russell; Drouard, David; Hoople, David; Jessiman, Alan; Miller, Duncan; Pasquinet, Christelle; Patel, Bhairavi; Reeves, Keith; Ryckmans, Thomas; Skerten, Melanie; Wakenhut, Florian Tetrahedron Letters, 2009 , vol. 50, # 4 p. 389 - 391

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 76.07
LogP 0.7069
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Morpholine compounds

Key Words

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(s)-4-(tert-butoxycarbonyl)Morpholine-2-carboxylic acid

CAS No. 868689-63-8

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