Hydrochloric Acid → HCID 42634449, compound

HRID 2064540Notes

Reaction equation

C(OC([N:8]([CH2:35][C:36]1[CH:37]=[C:38]([CH:52]=[CH:53][CH:54]=1)[C:39]([O:41][CH2:42][O:43]/[N:44]=[N+:45](\[O-:51])/[N:46]([CH2:49][CH3:50])[CH2:47][CH3:48])=[O:40])[S:9]([C:12]1[CH:17]=[C:16]([C:18]([NH:20][N:21]2[C:29]3[C:24](=[CH:25][C:26]([N+:30]([O-:32])=[O:31])=[CH:27][CH:28]=3)[CH2:23][CH:22]2[CH3:33])=[O:19])[CH:15]=[CH:14][C:13]=1[Cl:34])(=[O:11])=[O:10])=O)(C)(C)C.Cl.O>O1CCOCC1>[Cl:34][C:13]1[CH:14]=[CH:15][C:16]([C:18](=[O:19])[NH:20][N:21]2[C:29]3[C:24](=[CH:25][C:26]([N+:30]([O-:32])=[O:31])=[CH:27][CH:28]=3)[CH2:23][CH:22]2[CH3:33])=[CH:17][C:12]=1[S:9]([NH:8][CH2:35][C:36]1[CH:37]=[C:38]([CH:52]=[CH:53][CH:54]=1)[C:39]([O:41][CH2:42][O:43]/[N:44]=[N+:45](\[O-:51])/[N:46]([CH2:47][CH3:48])[CH2:49][CH3:50])=[O:40])(=[O:10])=[O:11]

Participants

Conditions

Temperature: 70 °C

Procedure

Dissolve the compound obtained in Step D (4.38×10−4 mol) in dioxane (25 ml). Place under stirring and then add 37% hydrochloric acid (3.5 ml) and heat at 70° C. After 2 hours, the reaction mixture is poured into water (50 ml). Extract 3 times with ethyl acetate (20 ml). The organic phase is washed with water and then with brine, dried over magnesium sulphate, filtered and concentrated using a rotary evaporator. The oily orange-coloured crude product obtained is chromatographed on a silica column using as eluant a 60/40 n-heptane/ethyl acetate mixture.

Workup

extractionExtract 3 times with ethyl acetate (20 ml)
washThe organic phase is washed with water
dry with materialwith brine, dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated
customa rotary evaporator

Sources & evidence

ORD record: ord-f53f51092eaa4295b0b6f8de732903c9
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288433B2

Reaction notes

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