1,2-Dichloroethane → HCID 58355688, compound

HRID 1509551Notes

Reaction equation

[N+:1](=[C:3]([C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[C:4]([O:6][CH3:7])=[O:5])=[N-].[C:16]1([NH:22][C:23](N)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ClCCCl.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Rh+4]>[CH3:14][O:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]1[N:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:23](=[O:24])[NH:1][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 2-diazo-7-methoxy-3-oxoheptanoate (6.93 g) and 1-phenylurea (5.41 g) were suspended in toluene (30 ml)-1,2-dichloroethane (30 ml), rhodium tetraacetate (230 mg) was added and the mixture was stirred at 80° C. for 2 hr. After cooling to room temperature, trifluoroacetic acid (7.5 ml) was added and the reaction mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (15:85-100:0) was concentrated under reduced pressure to give the object product (7.40 g).

Workup

additionwas added
temperatureAfter cooling to room temperature
stirringthe reaction mixture was stirred at room temperature for 1 day
concentrationThe reaction mixture was concentrated under reduced pressure
washa fraction eluted with ethyl acetate-hexane (15:85-100:0)
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-89e7d509e3414b2c8587c9e4872aeab8
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221836B2

Reaction notes

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