Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate → 1-[[4-[4-[3-[3-(Trifluoromethyl)phenyl]but-2-enoyl]phenyl]phenyl]methyl]azetidine-3-carboxylic acid

HRID 717673Notes

Reaction equation

HRID 717673 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22](=[O:36])[CH:23]=[C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=4)[CH3:25])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6]1)=[O:4].COC(C1CN(CC2C=CC(OCC3C4C=C(Cl)C=CC=4OC=3)=CC=2)C1)=O>>[F:35][C:32]([F:33])([F:34])[C:28]1[CH:27]=[C:26]([C:24]([CH3:25])=[CH:23][C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:14]=[CH:15][C:10]([CH2:9][N:7]4[CH2:8][CH:5]([C:3]([OH:4])=[O:2])[CH2:6]4)=[CH:11][CH:12]=3)=[CH:21][CH:20]=2)=[O:36])[CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 66614996Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylateHCID 68002037Methyl-1-((4'-(3-(3-(trifluoromethyl)phenyl)but-2-enoyl)biphenyl-4-yl)methyl)azetidine-3-carboxylate

Product 1

HCID 666150491-[[4-[4-[3-[3-(Trifluoromethyl)phenyl]but-2-enoyl]phenyl]phenyl]methyl]azetidine-3-carboxylic acidYield 62%

Procedure

When the product of Step E was substituted for methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate in Example 25, Step E, the similar process afforded the title compound in 62% yield, as a light yellow solid. 1H-NMR (CDCl3+CD3OD) 7.84 (d, 2H, J=8.34 Hz); 7.59-7.33 (m, 6H); 4.7 (d, 2H); 3.96-3.92 (m, 4H); 3.19-3.14 (m, 1H); 2.36 (s, 3H).

Sources & evidence

ORD record
ord-78f5768646dc4f32af7557f69bed6d26
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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