Boc-Beta-iodo-Ala-Ome Chemical Properties

Melting point:

50-52 °C(lit.)

Boiling point:

356.5±32.0 °C(Predicted)

Density 

1.551±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

pka

10.44±0.46(Predicted)

form 

Powder

color 

White to yellow

optical activity

[α]22/D 4°, c = 2 in methanol

Water Solubility 

Soluble in water and 1% acetic acid.

Sensitive 

Light Sensitive

BRN 

4422011

InChI

InChI=1S/C9H16INO4/c1-9(2,3)15-8(13)11-6(5-10)7(12)14-4/h6H,5H2,1-4H3,(H,11,13)/t6-/m0/s1

InChIKey

UGZBFCCHLUWCQI-LURJTMIESA-N

SMILES

C(OC)(=O)[C@H](CI)NC(OC(C)(C)C)=O

CAS DataBase Reference

93267-04-0

Safety Information

Safety Statements 

24/25

WGK Germany 

3

F 

8

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

Boc-Beta-iodo-Ala-Ome Usage And Synthesis

Uses

N-Boc-3-iodo-L-alanine methyl ester is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropionate from methyl Boc-L-serinate: a mixture of triphenylphosphine (131 g, 0.500 mol) and imidazole (34 g, 0.50 mol) in dichloromethane (600 mL) was cooled to 0 °C and over 0.5 h iodine was added in batches (127 g, 0.50 mol). The cooling bath was removed and the mixture was stirred for 0.5 hours. After cooling the mixture to 0 °C again, a solution of methyl (R)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropionate (73 g, 0.33 mol) in dichloromethane (300 mL) was slowly added dropwise. After dropwise addition, the cooling bath was removed and the mixture was warmed to room temperature and stirred for 1.5 hours. The reaction mixture was filtered and the filtrate was concentrated to remove most of the solvent. Methyl tert-butyl ether (400 mL) was added to the residue and filtered to remove triphenylphosphine oxide. The filtrate was concentrated and the residue was purified by rapid column chromatography on silica gel to afford methyl (R)-2-((tert-butoxycarbonyl)amino)-3-iodopropionate (74.0 g, 68% yield) as a colorless solid.

References

[1] Journal of Organic Chemistry, 2009, vol. 74, # 17, p. 6792 - 6796
[2] Organic Letters, 2003, vol. 5, # 24, p. 4599 - 4602
[3] Organic Letters, 2011, vol. 13, # 10, p. 2614 - 2617
[4] Tetrahedron, 2017, vol. 73, # 42, p. 6085 - 6091
[5] Tetrahedron Letters, 2007, vol. 48, # 16, p. 2857 - 2859

Boc-Beta-iodo-Ala-Ome(93267-04-0)Related Product Information

• PRND
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• 1-Boc-3-iodoazetidine
• DABSYL-L-ALANINE