3-[(Benzyloxycarbonyl)amino]propionaldehyde

Bezeichnung:3-[(Benzyloxycarbonyl)amino]propionaldehyde

CAS-Nr65564-05-8

Englisch Name:3-[(Benzyloxycarbonyl)amino]propionaldehyde

CBNumberCB8366386

SummenformelC11H13NO3

Molgewicht207.23

MOL-Datei65564-05-8.mol

3-[(Benzyloxycarbonyl)amino]propionaldehyde physikalisch-chemischer Eigenschaften

Schmelzpunkt	52-57 °C (lit.)
Siedepunkt	370.1±35.0 °C(Predicted)
Dichte	1.142±0.06 g/cm3(Predicted)
storage temp.	2-8°C
Aggregatzustand	Crystalline Powder
pka	12.08±0.46(Predicted)
Farbe	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 Datenbank	65564-05-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
WGK Germany	3
HS Code	29223900
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

3-[(Benzyloxycarbonyl)amino]propionaldehyde Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
White to yellow crystalline powder
Verwenden
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.
Synthese

34637-22-4

65564-05-8

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 Celitefilter. 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.
Einzelnachweise
[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

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