Dimethyl Sulfoxide → HCID 140365319, compound

HRID 1590271Notes

Reaction equation

[OH:1]/[N:2]=[C:3](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1)\[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-:35].[K+].[K+].[C:40](OC(=O)C(Br)C)(C)(C)[CH3:41].CS(C)=O.[CH2:54]([O:56][CH2:57][CH3:58])[CH3:55]>>[CH2:54]([O:56][C:57]([CH2:58][O:1]/[N:2]=[C:3](/[C:9]1[N:10]=[C:11]([NH:14][C:15]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1)\[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:35])[CH2:55][CH2:40][CH3:41]

Participants

Reactant 5

HCID 679Dimethyl Sulfoxide

HCID 3283Diethyl Ether

HCID 11430Potassium Carbonate

HCID 545327tert-Butyl 2-bromopropanoate

HCID 6410761(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetate

Product 1

HCID 140365319HCID 140365319, compound

Procedure

To ethyl (Z)-2-(hydroxyimino)-2-[2-(triphenylmethyl)aminothiazol-4-yl]acetate(46 g) were added potassium carbonate(27.6 g), tert-butyl-2-bromopropionate(20 g) and dimethylsulfoxide(300 ml). The reaction mixture was stirred for 5 hours at room temperature, followed by addition of ethyl ether (2 l). After the reaction mixture was washed 5 times with distilled water(500 ml), the separated organic layer was dehydrated and concentrated to give the above-indicated compound(47.2 g) in a yellow solid.

Workup

washAfter the reaction mixture was washed 5 times with distilled water(500 ml)
concentrationconcentrated

Sources & evidence

ORD record: ord-9d64ce01ea994784908c572e8c1c7a6e
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05202315

Reaction notes

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