(2R,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID Chemical Properties

Melting point:

123°C

Boiling point:

390.9±42.0 °C(Predicted)

Density 

1.312±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

3.80±0.40(Predicted)

form 

solid

color 

White

optical activity

[α]/D +70°, c = 0.617 g/mL in methanol

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

(2R,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID Usage And Synthesis

Chemical Properties

White powder

Uses

Boc protected Proline derivative.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of N-BOC-trans-4-hydroxy-D-proline from di-tert-butyl dicarbonate and L-hydroxyproline: Step A: Preparation of (4β)-1-Boc-4-hydroxy-L-proline 1. dissolve L-hydroxyproline (5.08 g, 38.77 mmol) in a solvent mixture of 1N NaOH solution (40 mL) and 1,4-dioxane (40 mL). 2. Di-tert-butyl dicarbonate (9.3 g, 42.6 mmol) was added drop-wise to the above solution at 0 °C. 3. The reaction mixture was stirred at room temperature for 8 hours. 4. 4. After completion of the reaction, the mixture was concentrated under vacuum to remove the solvent. 5. The concentrated mixture was acidified with 1N HCl and then extracted with EtOAc. 6. The organic extract was washed with brine, dried over MgSO4 and filtered. 7. Finally, the filtrate was concentrated under vacuum to give N-BOC-trans-4-hydroxy-D-proline (8.84 g, 99% yield). MS [M + H] = 232 (M + 1).

IC 50

Non-cleavable Linker

References

[1] Patent: WO2010/56022, 2010, A2. Location in patent: Page/Page column 21

(2R,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID(147266-92-0)Related Product Information

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• (R)-2-Aminomethyl-4-boc-morpholine
• (S)-tert-Butyl 4,4-difluoro-2-(hydroxymethyl)-pyrrolidine-1-carboxylate
• (2R,4R)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
• Boc-Hyp-OH
• N-Boc-trans-4-Hydroxy-L-proline methyl ester
• (2S,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
• N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER
• trans-4-Hydroxy-D-proline
• BOC-TRANS-HYP-OH,BOC-L-HYP-OH,(2S,4R)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID