Bromopinacolone → HCID 45111067, compound

HRID 468589Notes

Reaction equation

HRID 468589 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:16])[C:12]([O:14]C)=[O:13])=[CH:7][CH:6]=1)(=[S:3])[NH2:2].Br[CH2:18][C:19](=O)[C:20]([CH3:23])([CH3:22])[CH3:21]>>[C:20]([C:19]1[N:2]=[C:1]([NH:4][C:5]2[CH:10]=[CH:9][C:8]([CH:11]([CH3:16])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=2)[S:3][CH:18]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 21642BromopinacoloneHCID 86657119HCID 86657119, compound2×

Product 1

HCID 45111067HCID 45111067, compoundYield 57%

Procedure

Following the same procedure described for 1 and starting from methyl 2-[4-(carbamothioylamino)phenyl]propanoate (2.49 g, 10 mmol) and 1-bromopinacolone (1.75 ml, 13 mmol), after workup and methyl ester hydrolysis, pure compound 6 (1.75 g, 5.7 mmol) was isolated by filtration (38% overall yield from methyl 2-[4-(carbamothioylamino)phenyl]propanoate).

Sources & evidence

ORD record
ord-588ce454ad984c159e1bfed1ca5467fc
Source dataset
uspto-grants-2014_01
Patent number
US08624036B2

Reaction notes

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