BOC-HYP-OL Chemical Properties

Melting point:

81-86 °C (lit.)

alpha 

-47o (C=1 IN CHLOROFORM)

Boiling point:

340.3±27.0 °C(Predicted)

Density 

1.190±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

14.57±0.40(Predicted)

color 

White

optical activity

[α]20/D 47°, c = 1 in chloroform

Sensitive 

Air Sensitive

InChI

InChI=1S/C10H19NO4/c1-10(2,3)15-9(14)11-5-8(13)4-7(11)6-12/h7-8,12-13H,4-6H2,1-3H3/t7-,8+/m0/s1

InChIKey

UFJNFQNQLMGUTQ-JGVFFNPUSA-N

SMILES

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

CAS DataBase Reference

61478-26-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

BOC-HYP-OL Usage And Synthesis

Chemical Properties

Viscous Oil

Uses

BOC-HYP-OL is a useful reactant used in the preparation of 4-purinylpyrrolidine nucleosides, kinase inhibitors and antibacterial agents.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Under argon protection, 1-tert-butyl 2-methyl-(2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate (5.0 g, 20.41 mmol) was dissolved in THF (100 mL), cooled to -16 °C and stirred. LiAlH4 (1 M solution of THF, 21 mL, 21 mmol) was added slowly and dropwise over 5 min and precipitate formation was observed in the reaction. THF (50 mL) was subsequently added to destroy the precipitate. The reaction mixture was gradually warmed to 0 °C with stirring for 3.5 hours. Upon completion of the reaction, the reaction was quenched with EtOAc (5 mL) and stirring was continued for 30 minutes. Then, an excess of Rochelle's salt solution (100 mL) was carefully added, and the mixture was warmed to room temperature and stirred for an additional 1 hour. The mixture was extracted twice with CH2Cl2 (100 mL), the organic phases were combined, dried with MgSO4, filtered and concentrated under reduced pressure to remove the solvent. The product was purified by column chromatography (eluent: 10% MeOH/CH2Cl2) to give Intermediate 19 in quantitative yield.1H NMR (300 MHz, DMSO-d6) δ: 4.82 (br s, 1H), 4.64 (br d, J = 5.5 Hz, 1H), 4.20 (sxt, J = 4.2 Hz, 1H), 3.75 (br s , 1H), 3.16-3.50 (m, 4H), 1.85-2.02 (m, 1H), 1.80 (br s, 1H), 1.39 (s, 9H).

References

[1] Patent: WO2017/29521, 2017, A1. Location in patent: Page/Page column 37
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2787 - 2797
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 1, p. 56 - 60
[4] Patent: US2014/256016, 2014, A1. Location in patent: Paragraph 0024; 0025
[5] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 294 - 296

BOC-HYP-OL(61478-26-0)Related Product Information

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