Hydrochloric Acid → HCID 54196894, compound

HRID 369874Notes

Reaction equation

[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.[CH3:13][O:14][C:15]1[CH:34]=[C:33]([CH:35]=[O:36])[CH:32]=[CH:31][C:16]=1[O:17][CH2:18][C:19]([NH:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1)=[O:20].Cl>O1CCCC1.CCCCCC.O>[CH3:13][O:14][C:15]1[CH:34]=[C:33]([CH:35]([OH:36])[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4])[CH:32]=[CH:31][C:16]=1[O:17][CH2:18][C:19]([NH:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1)=[O:20]

Participants

Conditions

Temperature: -50 °C

Procedure

To a solution of dimethyl methylphosphonate (19.5 ml) in anhydrous tetrahydrofuran (300 ml) is added a 1.72 M solution of n-butyl lithium in n-hexane (107 ml) at -50° C. Thirty minutes later, to the mixture is added in portions 2-(2-methoxy-4-formylphenoxymethylcarbonylamino)benzothiazole (20.5 g) under nitrogen atmosphere. The mixture is stirred at -50° C. for one hour, and thereto is added water. The mixture is acidified with conc. hydrochloric acid, and extracted with ethyl acetate. The extract is washed with water, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=200:1→30:1) to give dimethyl {2-[3-methoxy-4-(2-benzothiazolylaminocarbonylmethoxy)phenyl]-2-hydroxyethyl}phosphonate (19.0 g).

Workup

extractionextracted with ethyl acetate
washThe extract is washed with water
customdried
concentrationconcentrated under reduced pressure
customThe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=200:1→30:1)

Sources & evidence

ORD record: ord-f09fa7b2335a4461a2226933aa536848
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06140330

Reaction notes

Loading…