N-Hydroxysuccinimide → N-{4-[2-[bis(2-chloroethyl)amino]phenyl]butyroyl}-4-aminobutane-1,1-diphosphonic acid tetraethyl ester

HRID 1463543Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][N:4]([CH2:17][CH2:18][Cl:19])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O.ON1C(=O)CCC1=O.[CH2:28]([O:30][P:31]([CH:36]([P:41]([O:46][CH2:47][CH3:48])(=[O:45])[O:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH2:39][NH2:40])(=[O:35])[O:32][CH2:33][CH3:34])[CH3:29]>>[CH2:43]([O:42][P:41]([CH:36]([P:31]([O:30][CH2:28][CH3:29])(=[O:35])[O:32][CH2:33][CH3:34])[CH2:37][CH2:38][CH2:39][NH:40][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[N:4]([CH2:3][CH2:2][Cl:1])[CH2:17][CH2:18][Cl:19])(=[O:45])[O:46][CH2:47][CH3:48])[CH3:44]

Participants

Reactant 3

HCID 80170N-Hydroxysuccinimide

HCID 238870Ortho-chlorambucil

HCID 153967084,4-Bis(diethoxyphosphoryl)butan-1-amine

Product 1

HCID 86747738N-{4-[2-[bis(2-chloroethyl)amino]phenyl]butyroyl}-4-aminobutane-1,1-diphosphonic acid tetraethyl ester

Procedure

Following the procedure described in Example 1b), by reacting 4-[2-[bis(2-chloroethyl)amino]phenyl]butyric acid (J. Org. Chem. 26, 1554, (1961)) with N-hydroxysuccinimide and N-morpholinoethylisonitrile, 4-[2-[bis(2-chloroethyl)amino]phenyl]butyric acid N-hydroxysuccinimido ester is prepared. Said N-hydroxysuccinimido ester is reacted with 4-aminobutane-1,1-diphosphonic acid tetraethyl ester, according to the procedure described in Example 10, to give N-{4-[2-[bis(2-chloroethyl)amino]phenyl]butyroyl}-4-aminobutane-1,1-diphosphonic acid tetraethyl ester, which is reacted with iodotrimethylsilane, following the procedure described in Example 11, to obtain N-{4-[2-[bis(2-chloroethyl)amino]phenyl]butyroyl}-4-aminobutane-1,1-diphosphonic acid disodium salt.

Workup

customis prepared

Sources & evidence

ORD record: ord-96359cbce91b4174beb33422e8d14817
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05300671

Reaction notes

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