Allyl bromide → HCID 67305114, compound

HRID 1865453Notes

Reaction equation

HRID 1865453 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH2:5]([NH:12][C:13](=[O:35])[N:14]([C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C@H:29]([OH:34])[C:30]([O:32][CH3:33])=[O:31])=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1)[CH3:15])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>C(OCC)C.[Ag]=O>[CH2:1]([O:34][C@@H:29]([CH2:28][C:25]1[CH:24]=[CH:23][C:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([N:14]([CH3:15])[C:13]([NH:12][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:35])[CH:17]=2)=[CH:27][CH:26]=1)[C:30]([O:32][CH3:33])=[O:31])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 7841Allyl bromideHCID 67304495HCID 67304495, compound

Product 1

HCID 67305114HCID 67305114, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

58 μl (0.70 mmol) of allyl bromide are added to a mixture of 162 mg (0.70 mmol) of silver oxide and 200 mg (0.47 mmol) of methyl (S)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]-2-hydroxypropanoate in 3 ml of diethyl ether. The reaction mixture is stirred at 40° C. for 24 hours. The mixture is filtered and then the solvents are evaporated. The residue is chromatographed on silica gel (heptane/ethyl acetate 80/20 up to 60/40). 180 mg of methyl (S)-2-allyloxy-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate are obtained in the form of an oil. Yield=82%.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvents are evaporated
  3. customThe residue is chromatographed on silica gel (heptane/ethyl acetate 80/20 up to 60/40)

Sources & evidence

ORD record
ord-495f864df1314e21bc644199b8c15f38
Source dataset
uspto-grants-2009_12
Patent number
US07626054B2

Reaction notes

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