(R)-4-BOC-THIOMORPHOLINE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

145-146

Boiling point:

398.6±42.0 °C(Predicted)

Density 

1.259±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

3.53±0.20(Predicted)

Appearance

Off-white to brown Solid

optical activity

-0.74°(C=1.0 g/100ml MEOH)

InChI

InChI=1S/C10H17NO4S/c1-10(2,3)15-9(14)11-4-5-16-6-7(11)8(12)13/h7H,4-6H2,1-3H3,(H,12,13)

InChIKey

CTDIKDIZNAGMFK-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCSCC1C(O)=O

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

Hazard Note 

Irritant

HS Code 

2934999090

(R)-4-BOC-THIOMORPHOLINE-3-CARBOXYLIC ACID Usage And Synthesis

Synthesis

The general procedure for the synthesis of N-Boc-3-thiomorpholinecarboxylic acid from 1,4-dioxane, di-tert-butyl dicarbonate and 3-thiomorpholinecarboxylic acid is as follows: (a) Synthesis of 4-(tert-butoxycarbonyl)thiomorpholine-3-carboxylic acid: triethylamine (23.6 mL) was slowly added to a solution of DL-thiomorpholine-3-carboxylic acid (5 g) dissolved in 40 mL of a solvent mixture of 1,4-dioxane and water (1:1, v/v) at 0 °C. Subsequently, di-tert-butyl dicarbonate (8.16 g) was added and the reaction mixture was stirred at 0 °C for 30 min and then continued for 3 h at room temperature. After completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was dissolved in 100 mL of ethyl acetate. The pH of the reaction solution was adjusted to 4 with saturated citric acid solution and then extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized by hexane/ethyl acetate mixed solvent to give 4-(tert-butoxycarbonyl)thiomorpholine-3-carboxylic acid (6.0 g, 71% yield).

References

[1] Patent: US5021413, 1991, A

(R)-4-BOC-THIOMORPHOLINE-3-CARBOXYLIC ACID(128453-98-5)Related Product Information

• Thiomorpholine
• Thiomorpholine-3-carboxylic acid
• 4-N-BOC-THIOMORPHOLINE-3-CARBOXYLIC ACID
• (S)-4-BOC-THIOMORPHOLINE-3-CARBOXYLIC ACID
• N-BOC-THIOMORPHOLINE-3-CARBOXYLIC ACID ETHYL ESTER
• N-BOC-THIOMORPHOLINE-3-CARBOXYLIC ACID ETHYL ESTER
• (R)-4-BOC-THIOMORPHOLINE-3-CARBOXYLIC ACID
• (R)-4-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLTHIOMORPHOLINE-3-CARBOXYLIC ACID
• (R)-4-BOC-THIOMORPHOLINE-3-CARBOXYLIC ACID