| Identification | Back Directory | [Name]
BOC-ALA-ALA-OH | [CAS]
27317-69-7 | [Synonyms]
Boc-AA-OH
Boc-Ala-Ala
BOC-ALA-ALA-OH
BOC-ALA-ALA-OH H2O
Boc-L-Ala-L-Ala-OH
BOC-L-ALANYL-L-ALANINE H2O
BOC-L-ALANYL-L-ALANINE MONOHYDRATE
N-tert-Butoxycarbonyl-L-alanyl-L-alanine
(tert-Butoxycarbonyl)-L-alanyl-L-alanine
L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-
(2S)-2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}propanamido]propanoic acid | [EINECS(EC#)]
421-060-8 | [Molecular Formula]
C11H20N2O5 | [MDL Number]
MFCD00038564 | [MOL File]
27317-69-7.mol | [Molecular Weight]
260.29 |
| Chemical Properties | Back Directory | [Melting point ]
132-133 °C | [Boiling point ]
483.5±30.0 °C(Predicted) | [density ]
1.163±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
3.52±0.10(Predicted) | [color ]
White to Off-White | [Stability:]
Hygroscopic | [InChI]
1S/C11H20N2O5/c1-6(8(14)12-7(2)9(15)16)13-10(17)18-11(3,4)5/h6-7H,1-5H3,(H,12,14)(H,13,17)(H,15,16)/t6-,7-/m0/s1 | [InChIKey]
BZNDDHWTEVCBAD-BQBZGAKWSA-N | [SMILES]
C[C@H](NC(=O)[C@H](C)NC(=O)OC(C)(C)C)C(O)=O |
| Hazard Information | Back Directory | [Uses]
N-Phthalyl-alanine is used in the preparation of endothiopeptide inhibitors of HIV-1 Protease. | [Synthesis]
GENERAL STEPS: L-alanyl-L-alanine (1 mmol) was slowly added to a solution of ethanol (1 mL) containing guanidine hydrochloride (15 mmol) and di-tert-butyl dicarbonate (2.5-3 mmol) under stirring conditions, maintaining the reaction temperature at 35-40°C. The reaction mixture was stirred continuously until a clarified solution was formed. Subsequently, the ethanol was removed by evaporation under reduced pressure. The residue was washed sequentially with distilled water (2 mL) and hexane or petroleum ether (2 mL) to obtain nearly pure N-tert-butoxycarbonyl-alanylalanine. If further product purity is required, the crude product can be purified by recrystallization. | [References]
[1] Journal of Organic Chemistry, 2007, vol. 72, # 2, p. 525 - 531
[2] Journal of the American Chemical Society, 2000, vol. 122, # 12, p. 2687 - 2697
[3] Journal of Organic Chemistry, 1994, vol. 59, # 19, p. 5784 - 5793
[4] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1260 - 1264
[5] Journal of Medicinal Chemistry, 2005, vol. 48, # 16, p. 5305 - 5320 |
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