Ifosfamide synthesis

5synthesis methods

Product Name:Ifosfamide
CAS Number:3778-73-2
Molecular formula:C7H15Cl2N2O2P
Molecular Weight:261.09

Ifosfamide, 3-(2-chloroethyl)-2-[(2-chloroethyl)amino]tetrahydro-2H-1,3,2- oxazaphosphorin-2-oxide (30.2.1.17), which is viewed as an isomeric compound of cyclophosphamide (30.2.1.15) and which is analogous in terms of action, is made by reacting N-(2-chloroethyl)-N-(3-hydroxypropyl)amine with phosphorous oxychloride, giving 3-(2-chloroethyl)-2-chlorotetrahydro-2H-1,3,2-oxazaphosphorin-2-oxide (30.2.1.16), which is reacted with N-(2-chloroethyl)amine, forming the desired ifosfamide (30.2.1.17).

2H-1,3,2-Oxazaphosphorine, 2-(1-aziridinyl)-3-(2-chloroethyl)tetrahydro-, 2-oxide

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Yield:3778-73-2 78%

Reaction Conditions:

with hydrogenchloride in chloroform

Steps:

V 2-(2-chloroethylamino)-2-oxo-3-(2-chloroethyl)-1.3.2-oxazaphosphorinane
EXAMPLE V 2-(2-chloroethylamino)-2-oxo-3-(2-chloroethyl)-1.3.2-oxazaphosphorinane Into the stirred solution of 2-ethyleneimino-2-oxo-3-(2-chloroethyl)-1.3.2-oxazaphosphorinane (1.12 g, 5.0 mM) in chloroform (12 ml) was added at room temperature dropwise 3% aq. solution of hydrogen chloride (6 mL, 5.0 mM). Stirring was continued for 15 min, organic layer separated and aquous layer extracted with chloroform (2*6 mL). Organic layers were combined together, dried over anhydrous MgSO₄. Removal of solvent under reduced pressure left a residue which upon crystallization from ether-n-pentane gave 1.02 g of crystalline product, mp. 45°-46° C. in 78% yield. δ₃₁_P =11.3 ppm (CHCl₃). Mass spectrum m/e: 262 (0.3%), 260 (0.3%), 260 (0.8%), 213 (37%), 211 (100%).

References:

Polska Akademia Nauk-Centrum Baden Molekularnych i Makromolekularnych US4684742, 1987, A

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81485-04-3 Synthesis