4-Boc-3(S)-morpholinecarboxylic acid Chemical Properties

Boiling point:

369.5±42.0 °C(Predicted)

Density 

1.230±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

pka

3.53±0.20(Predicted)

form 

powder

color 

White

optical activity

Consistent with structure

InChI

InChI=1S/C10H17NO5/c1-10(2,3)16-9(14)11-4-5-15-6-7(11)8(12)13/h7H,4-6H2,1-3H3,(H,12,13)/t7-/m0/s1

InChIKey

KVXXEKIGMOEPSA-ZETCQYMHSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCOC[C@H]1C(O)=O

Safety Information

HS Code 

2934999090

4-Boc-3(S)-morpholinecarboxylic acid Usage And Synthesis

Uses

(S)-4-Boc-morpholine-3-carboxylic Acid is used to prepare indazole arylsulfonamides as allosteric CC-chemokine receptor 4 antagonists.

Synthesis

The general procedure for the synthesis of (3S)-4-tert-butyl 3,4-morpholine dicarboxylate from 3-morpholinecarboxylic acid and di-tert-butyl dicarbonate was as follows: to a solution of dichloromethane (DCM, 100 mL) containing morpholine-3-carboxylic acid (3 g, 22.9 mmol, 1.0 eq.) was added sequentially triethylamine (TEA, 6.9 g, 68.7 mmol, 3.0 eq.) and di Di-tert-butyl carbonate (Boc2O, 15 g, 68.7 mmol, 3.0 eq.). The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was concentrated and the resulting residue was purified by silica gel column chromatography (eluent ratio petroleum ether/ethyl acetate = 5/1) to afford the target product (S)-4-(tert-butoxycarbonyl)morpholine-3-carboxylic acid (700 mg, 14% yield) as a colorless liquid.

References

[1] Patent: WO2017/98328, 2017, A2. Location in patent: Paragraph 00266

4-Boc-3(S)-morpholinecarboxylic acid(783350-37-8)Related Product Information

• Methyl acrylate
• tert-Butanol
• tert-Butyl acrylate
• tert-Butyl methacrylate
• tert-Butyl chloroacetate
• Ethyl 2-(Chlorosulfonyl)acetate
• tert-Butyl bromoacetate
• tert-Butyl acetate
• 2-Butoxyethanol
• Buprofezin
• tert-Butyl peroxyacetate
• Butyl acetate
• tert-Butyl acetoacetate
• Tris(trimethylsilyl)phosphate
• 4-Boc-3(R)-morpholinecarboxylic acid
• Butyl acrylate
• DI-TERT-BUTYL ETHER
• morpholine