Sodium Hydroxide → [4-(2-Acetoxybenzoyl)-amino-1-hydroxybutylidene]-diphosphonic acid

HRID 128913

Reaction equation

O.O.O.[NH2:4][CH2:5][CH2:6][CH2:7][C:8]([P:14](=[O:17])([OH:16])[OH:15])([P:10](=[O:13])([O-:12])[OH:11])[OH:9].[Na+].[OH-].[Na+].[C:21]([O:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28])(=[O:23])[CH3:22]>O.CN(C)C1C=CN=CC=1.[I-].C([N+](CCCCCC)(CCCCCC)CCCCCC)CCCCC.C(OCC)C>[C:21]([O:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([CH:5]([NH2:4])[CH2:6][CH2:7][C:8]([P:14](=[O:15])([OH:16])[OH:17])([P:10](=[O:11])([OH:12])[OH:13])[OH:9])=[O:28])(=[O:23])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

3.18 g (9.8 mmoles ) of sodium trihydrogen 4-amino-1-hydroxybutylidenediphosphonate trihydrate are added in 30 ml of water to 1.8 g (45 mmoles) of sodium hydroxide, 100 mg of p-dimethylaminopyridine and 200 mg of tetrahexylammonium iodide. The resulting solution is cooled to 0° C., and added with 2.03 g (10.2 mmoles) of 2-acetoxybenzoic acid chloride dissolved in 10 ml of diethyl ether. The reaction mixture is stirred for 2 hours at room temperature, then it is extracted with ethyl ether and the aqueous solution is acidified with concentrated HCl under stirring, with cooling. [4-(2-Hydroxybenzoyl)-amino-1-hydroxybutylidene]-diphosphonic acid precipitates, which is filtered, washed and dried at 70° C. and transformed into the title product by means of acetylation with acetic anhydride.

Workup

extractionit is extracted with ethyl ether
stirringunder stirring
temperaturewith cooling
custom[4-(2-Hydroxybenzoyl)-amino-1-hydroxybutylidene]-diphosphonic acid precipitates
filtrationwhich is filtered
washwashed
customdried at 70° C.

Sources & evidence

ORD record: ord-000990f6f7624768a2d521f93c51d0f7
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05466682

Linked notes

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