N-Boc-cis-4-Hydroxy-L-proline Chemical Properties

Melting point:

146 °C (D) (lit.)

alpha 

-50 º (c=0.67, MeOH)

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

form 

Powder or Crystalline Powder

pka

3.80±0.40(Predicted)

color 

White to off-white

optical activity

[α]20/D -50.0±3°, c = 0.67 in methanol

InChI

InChI=1S/C10H17NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h6-7,12H,4-5H2,1-3H3,(H,13,14)/t6-,7-/m0/s1

InChIKey

BENKAPCDIOILGV-BQBZGAKWSA-N

SMILES

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

CAS DataBase Reference

87691-27-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50

Safety Statements 

26-36/37-60-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

N-Boc-cis-4-Hydroxy-L-proline Usage And Synthesis

Chemical Properties

White powder

Uses

peptide synthesis

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of N-Boc-cis-4-hydroxy-L-proline from (S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid: An appropriate amount of solvent was added to the reaction vessel and cooled to the specified temperature. Subsequently, the reducing agent (4.0~5.0 equivalents) was added in batches, taking care to control the rate of addition to avoid violent exotherm. The progress of the reaction was monitored by HPLC during the reaction. Upon completion of the reaction, the reaction solution was slowly poured into ice water to maintain the temperature at 0~5°C. The pH was adjusted to 0~5°C with dilute hydrochloric acid. The pH was adjusted to 2~3 with dilute hydrochloric acid and then extracted with ethyl acetate (EA) (5X each time, 3 times). All organic phases were combined, washed with saturated brine and dried with anhydrous sodium sulfate. The dried organic phase was concentrated under reduced pressure to give the crude product. Finally, the crude product was recrystallized in a mixed solvent of ethyl acetate and alkanes to give purified N-Boc-cis-4-hydroxy-L-proline.

References

[1] Patent: CN106543062, 2017, A. Location in patent: Paragraph 0021; 0024; 0027
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2253 - 2265
[3] Tetrahedron Letters, 1993, vol. 34, # 46, p. 7489 - 7492
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 251 - 259

N-Boc-cis-4-Hydroxy-L-proline(87691-27-8)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• L-Hydroxyproline
• Glycine
• Folic acid
• CHLOROPHOSPHONAZO III
• BOC-L-Proline
• cis-4-Hydroxy-L-proline
• N-BOC-CIS-4-HYDROXY-L-PROLINE METHYL ESTER,N-T-BOC-CIS-4-HYDROXY-L-PROLINE METHYL ESTER,N-BOC-CIS-4-HYDROXY-L-PROLINE METHYL ES&
• D-Proline
• L-PROLINE-(4-3H(N))
• N-BOC-CIS-7-HYDROXY-D-PROLINE
• N-BOC-CIS-4-HYDROXY-D-PROLINE,N-T-BOC-CIS-4-HYDROXY-D-PROLINE,BOC-CIS-4-HYDROXY-D-PROLINE,N-BOC-CIS-6-HYDROXY-D-PROLINE
• (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-(2-NAPHTHYLOXY)-2-PYRROLIDINECARBOXYLIC ACID
• N-Boc-cis-4-Hydroxy-L-proline
• (2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-PHENOXY-2-PYRROLIDINECARBOXYLIC ACID
• CARBOXYLIC ACID
• N-T-BOC-CIS-3-HYDROXY-D-PROLINE,BOC-CIS-3-HYDROXY-D-PROLINE
• N-T-BOC-CIS-3-HYDROXY-L-PROLINE,BOC-CIS-3-HYDROXY-L-PROLINE