Benzyl Bromide → Methyl 3-[2-benzyloxy-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

HRID 250901Notes

Reaction equation

HRID 250901 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([NH:16][C:17](=[O:39])[N:18]([C:20]1[CH:21]=[C:22]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:28][C:27]=2[OH:38])[CH:23]=[CH:24][CH:25]=1)[CH3:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:1]([O:38][C:27]1[CH:28]=[C:29]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH:30]=[CH:31][C:26]=1[C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([N:18]([CH3:19])[C:17]([NH:16][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:39])[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11582687Methyl 3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate

Product 1

HCID 67272651Methyl 3-[2-benzyloxy-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a manner similar to that of Example (25a), by reaction of 300 μL (2.5 mmol, 2.7 eq) of benzyl bromide and 400 mg (0.93 mmol, 1 eq) of methyl 3-[3′-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate (prepared in Example 15f) in 10 ml of methyl ethyl ketone in the presence of 500 mg (3.61 mmol, 3.9 eq) of potassium carbonate at 90° C. for 3 hours, methyl 3-[2-benzyloxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate is obtained in oil form and is used in the following reaction without further purification.

Sources & evidence

ORD record
ord-42ded9a6d9bb4a3196985bb2983f42c8
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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