| Identification | Back Directory | [Name]
BOC-BETA-IODO-ALA-OME | [CAS]
93267-04-0 | [Synonyms]
A-OME
EOS-61913
-iodo-Ala-OMe
BOC-BETA-IODO-AL
Boc-Ala(3-I)-OMe
Boc-β-iodo-Ala-OMe
BOC-L-ALA(3-I)-OME
BOC-SS-IODO-ALA-OME
BOC-BETA-IODO-ALA-OME
(R)-Boc-β-Iodo-Ala-Ome
Boc-ß-iodo-Ala-OMe
Boc-beta-iodo-Ala-OMe 99%
(R)-N-Boc-Beta-Iodo-AlaOMe
BOC-BETA-IODO-ALA-OME USP/EP/BP
Boc-beta-iodo-ala-oMe“=LOWER(A1)
BOC-3-Iodo-L-alanine methyleester
N-boc-3-iodo-L-alanineMethylester
BOC-3-IODO-L-ALANINE METHYL ESTER
L-N-BOC-3-IODOALANINE METHYL ESTER
(Tert-Butoxy)Carbonyl β-Iodo-Ala-OMe
Boc-β-iodo-Ala-Ome, 98%, Boc-amino acids
3-Iodo-L-alanine methyl ester, N-BOC protected
N-(TERT-BUTOXYCARBONYL)-3-IODO-L-ALANINE METHYL ESTE
N-(TERT-BUTOXYCARBONYL)-3-IODO-L-ALININE METHYL ESTER
N-(TERT-BUTOXYCARBONYL)-3-IODO-L-ALANINE METHYL ESTER
tert-Butyl (R)-1-(methoxycarbonyl)-2-iodoethylcarbamate
N-(tert-Butoxycarbonyl)-3-iodo-L-alanine Methyl Ester >
Methyl(2R)-2-{[(tert-butoxy)carbony]Amino}-3-Iodopropanoate
L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-3-iodo-, methyl ester
L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-3-iodo-, methyl ester
(L)-2-TERT-BUTOXYCARBONYLAMINO-3-IODO-PROPIONIC ACID METHYL ESTER
(2R)-3-Iodo-2-(tert-butoxycarbonylamino)propanoic acid methyl ester
methyl (2R)-3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
(2R)-3-iodo-2-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]propanoic acid methyl ester
Boc-3-iodo-L-alanine methyl ester, N-(tert-Butoxycarbonyl)-3-iodo-L-alanine methyl ester | [Molecular Formula]
C9H16INO4 | [MDL Number]
MFCD00216579 | [MOL File]
93267-04-0.mol | [Molecular Weight]
329.13 |
| Chemical Properties | Back Directory | [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 | [form ]
Powder | [pka]
10.44±0.46(Predicted) | [color ]
White to yellow | [Optical Rotation]
[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 |
| Hazard Information | Back Directory | [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 |
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