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How to Prepare N-Benzyloxycarbonyl-L-proline?

How to Prepare N-Benzyloxycarbonyl-L-proline?
Mabel Answered Jul 26 2023

L-proline is an important amino acid for synthesizing human proteins and is a crucial raw material for amino acid infusion. N-Benzyloxycarbonyl-L-proline, as its N-protected compound, is a key intermediate in the synthesis of first-line antihypertensive drugs such as Captopril and Enalapril, and has been widely used in industries such as food and medicine. It can be used as a nutritional supplement and flavoring agent. When heated with sugar, it undergoes an amino acid-carbonyl reaction to produce unique aromatic substances.

Preparation

To prepare N-Benzyloxycarbonyl-L-proline, add 1200kg of toluene, 100kg of L-proline, and 88kg of sodium bicarbonate to a reaction vessel. Then, slowly add 178kg of benzyl chloroformate at 10-15°C over 1 hour. After completion, maintain the temperature at 15-20°C and stir for 2 hours. Heat the mixture to reflux, separate the water using a separator until no water flows out, cool the resulting solution to room temperature, filter, and dry to obtain the desired compound N-Benzyloxycarbonyl-L-proline [1].

Figure 1: Synthesis reaction of N-Benzyloxycarbonyl-L-proline

Figure 1: Synthesis reaction of N-Benzyloxycarbonyl-L-proline

Emergency Measures

First Aid:

Inhalation: If inhaled, move the patient to fresh air. Skin Contact: Remove contaminated clothing and thoroughly rinse the skin with soap and water. Seek medical attention if discomfort persists. Eye Contact: Separate the eyelids and rinse with flowing water or saline. Seek immediate medical attention. Ingestion: Rinse mouth and do not induce vomiting. Seek immediate medical attention.

Advice for the Protection of Rescuers:

Transfer the patient to a safe area. Consult a doctor. Show the safety data sheet of this chemical to the attending physician.

Firefighting Measures

Extinguishing Agents:

Use water mist, dry powder, foam, or carbon dioxide extinguishers. Avoid using a direct stream of water, as it may cause splashing of flammable liquids and spread the fire.

Firefighting Precautions and Protective Measures:

Firefighters must wear self-contained breathing apparatus and full firefighting gear while fighting the fire upwind. If possible, move the containers from the fire to an open area. Containers in the fire area that have changed color or emit sounds from safety relief devices must be evacuated immediately. Isolate the accident scene and prevent unauthorized personnel from entering. Contain and collect firefighting water to prevent environmental contamination.

Leakage Emergency Handling

It is recommended for emergency responders to wear self-contained breathing apparatus, antistatic clothing, and oil-resistant rubber gloves. Avoid contact or crossing over the leaked substance. All equipment used during the operation should be grounded. Cut off the leak source if possible. Eliminate all ignition sources. Establish a caution zone based on the area affected by liquid flow, vapor, or dust dispersion, and evacuate unrelated personnel to a safe area upwind or sideways.

References

[1] Takeuchi; Yamada; Suzuki; Koizumi. Tetrahedron, 1996, vol. 52, #1, pp. 225-232

 
N-Benzyloxycarbonyl-L-proline
1148-11-4
CAS No:1148-11-4
 
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