BOC-3,4-DEHYDRO-PRO-OH Chemical Properties

Melting point:

92-95℃

Boiling point:

336.4±42.0 °C(Predicted)

Density 

1.236

storage temp. 

2-8°C

pka

3.70±0.20(Predicted)

form 

powder

color 

white

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36-50

Safety Statements 

26-60-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HS Code 

2933 99 80

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

BOC-3,4-DEHYDRO-PRO-OH Usage And Synthesis

Chemical Properties

White to off-white crystalline powder

Uses

Boc-3,4-Dehydro-L-Proline is an N-terminal protected 3,4-Dehydro-L-proline. It is used in solid-phase peptide synthesis (SPPS) to make peptides. 3,4-Dehydro-L-proline is a alternate substrate of the amino acid oxidase, NikD.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Biochem/physiol Actions

Boc-3,4-Dehydro-L-Proline is an N-terminal protected amino acid used in solid-phase peptide synthesis (SPPS) to make peptides containing 3,4-Dehydro-L-proline.

Synthesis

3,4-Dehydro-L-proline (1.0 g, 8.8 mmol) was used as starting material and dissolved in a mixed solution of water (9.0 mL) and sodium bicarbonate (2.23 g, 26.5 mmol). Dioxane (9.0 mL) and di-tert-butyl dicarbonate (3.86 g, 17.7 mmol) were then added. The reaction mixture was stirred at room temperature overnight, after which the solvent was removed by concentration under reduced pressure. The concentrated residue was partitioned between ether (20 mL) and water (25 mL) to separate the organic and aqueous layers. The aqueous layer was diluted with ethyl acetate (20 mL) and acidified by slow addition of concentrated hydrochloric acid while stirring vigorously to precipitate and extract the product (S)-1-(tert-butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid into the organic layer. When the pH was reduced to about 2, the extraction was again carried out with ethyl acetate. The aqueous layer was treated with saturated sodium chloride solution and extracted a final time with ethyl acetate. All organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the target product (S)-1-(tert-butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid (2.0 g, 100% yield) as a colorless viscous oil.

References

[1] Patent: WO2008/24725, 2008, A1. Location in patent: Page/Page column 132

BOC-3,4-DEHYDRO-PRO-OH(51154-06-4)Related Product Information

• 3,4-DEHYDRO-DL-PROLINE
• BOC-SAR-OH
• BOC-N-Methyl-L-alanine
• 3,4-Dehydro-L-proline
• BOC-Glycine
• N-BOC-(METHYLAMINO)ACETALDEHYDE
• BOC-3,4-DEHYDRO-PRO-OH
• TERT-BUTYL N-ALLYLCARBAMATE
• 5-METHYL-2-PHENYL-1,3-OXAZOLE-4-CARBOXYLIC ACID
• N-Boc-pyrroline
• Methyl N-Boc-L-proline-3-ene
• ETHYL ALLYLFORMYLMETHYLCARBAMATE
• 1-(TERT-BUTOXYCARBONYL)-2,5-DIHYDRO-1H-PYRROLE-2-CARBOXYLIC ACID
• 2-AMINO-3-BUTENOIC ACID
• ALLYLAMINO-ACETIC ACID HYDROCHLORIDE
• L-VINYLGLYCINE
• 1-[(TERT-BUTYL)OXYCARBONYL]-4-PHENYLPYRROLINE-3-CARBOXYLIC ACID
• BOC-N-ETHYL GLYCINE