| Identification | More | [Name]
3-[(Benzyloxycarbonyl)amino]propionaldehyde | [CAS]
65564-05-8 | [Synonyms]
3-[(BENZYLOXYCARBONYL)AMINO]-1-PROPANAL
3-[(BENZYLOXYCARBONYL)AMINO]PROPIONALDEHYDE
N-Phenylmethoxycarbonyl-3-aminopropanol
N-Phenylmethoxycarbonyl-3-Aminopropanal
3-((BENZYLOXYCARBONYL)AMINO)-1-PROPANOL&
3-[(Benzyloxycarbonyl)amino]propionaldehyde, Benzyl (3-oxopropyl)carbamate
3-Aminopropanal, N-CBZ protected
3-[(Benzyloxycarbonyl)amino]-1-propanal, 3-[(Carbobenzyloxy)amino]propionaldehyde
3-Hydroxypropyl(benzyloxycarbonyl)amine
3-Hydroxypropylcarbamic acid benzyl ester | [Molecular Formula]
C11H13NO3 | [MDL Number]
MFCD05664298 | [Molecular Weight]
207.23 | [MOL File]
65564-05-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White to yellow crystalline powder | [Melting point ]
52-57 °C (lit.) | [Boiling point ]
370.1±35.0 °C(Predicted) | [density ]
1.142±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [form ]
Crystalline Powder | [pka]
12.08±0.46(Predicted) | [color ]
White to yellow | [InChI]
InChI=1S/C11H13NO3/c13-8-4-7-12-11(14)15-9-10-5-2-1-3-6-10/h1-3,5-6,8H,4,7,9H2,(H,12,14) | [InChIKey]
PQMOZOQTXKMYSK-UHFFFAOYSA-N | [SMILES]
C(OCC1=CC=CC=C1)(=O)NCCC=O | [CAS DataBase Reference]
65564-05-8(CAS DataBase Reference) | [Storage Precautions]
Store under inert gas;Air sensitive |
| Hazard Information | Back Directory | [Chemical Properties]
White to yellow crystalline powder | [Uses]
3-(Benzyloxycarbonylamino)propionaldehyde is used as a reagent in the synthesis of Tuberactinomycin N, a peptide antibiotic that is used as an anti-tuberculotic drug. 3-(Benzyloxycarbonylamino)propionaldehyde is also used as a reagent to prepare L-epicapreomycidine, a guanidino amino acid that is naturally found in hydrolyzates of protease inhibitors. | [Synthesis]
The general procedure for the synthesis of N-benzyloxycarbonyl-3-aminopropanal from 3-(benzyloxycarbonylamino)-1-propanol was as follows: PCC (8.75 g, 40.6 mmol, 1.7 eq.) and Celite? (9 g) were stirred in dichloromethane (50 mL) for 5 min, followed by the addition of 3-(benzyloxycarbonylamino)-1-propanol (5.0 g, 24 mmol) dissolved in dichloromethane (30 mL). propanol (5.0 g, 24 mmol). After 4 hours of reaction, the reaction mixture was diluted with ether (100 mL) and filtered through a short pad of silica gel and Celite?filter. The residual solid was suspended in dichloromethane (25 mL) and precipitated with ether (50 mL) to pass the mixture through the same filter pad. After this process was repeated three times, the filtrate was evaporated under reduced pressure to give a yellow oil (5.0 g). Purification by column chromatography (petroleum ether solution of 40% ethyl acetate) afforded N-benzyloxycarbonyl-3-aminopropionaldehyde as a colorless viscous oil (3.0 g, 14.5 mmol) in 60% yield. rf value of 0.4 (petroleum ether solution of 50% ethyl acetate, PMA color developed); 1H NMR (CDCl3) δ: 2.75 (2H, t, J=5.7Hz. CH2), 3.49 (2H, apparent q, J=6.0 Hz, CH2), 5.09 (2H, s, CH2), 5.15 (1H, br s, NH), 7.30-7.39 (5H, m, Ar), 9.81 (1H, s, CHO); 13C NMR (CDCl3) δ: 34.6, 44.2, 66.9, 128.2 , 128.3, 128.7, 136.5, 165.4, 201.3; IR (neat) νmax: 3445, 1704, 1645 cm-1. | [References]
[1] Tetrahedron Letters, 2001, vol. 42, # 2, p. 183 - 185
[2] European Journal of Organic Chemistry, 2012, # 17, p. 3270 - 3277
[3] Tetrahedron, 1997, vol. 53, # 37, p. 12391 - 12404
[4] Tetrahedron Letters, 1987, vol. 28, # 33, p. 3827 - 3830
[5] Synlett, 2017, vol. 28, # 13, p. 1554 - 1557 |
|
|