Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate → 1-(4-(4-oxo-2-phenyl-4H-chromen-6-yl)benzyl)azetidine-3-carboxylic acid

HRID 717676Notes

Reaction equation

HRID 717676 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:26]=[CH:25][C:15]([CH2:16][N:17]4[CH2:20][CH:19]([C:21]([O:23]C)=[O:22])[CH2:18]4)=[CH:14][CH:13]=3)[CH:10]=2)[O:5][C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:3]1.COC(C1CN(CC2C=CC(OCC3C4C=C(Cl)C=CC=4OC=3)=CC=2)C1)=O>>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:26]=[CH:25][C:15]([CH2:16][N:17]4[CH2:20][CH:19]([C:21]([OH:23])=[O:22])[CH2:18]4)=[CH:14][CH:13]=3)[CH:10]=2)[O:5][C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:3]1

Participants

3

Reactant 2

HCID 66614996Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylateHCID 66615050Methyl 1-(4-(4-oxo-2-phenyl-4H-chromen-6-yl)benzyl)azetidine-3-carboxylate

Product 1

HCID 461998291-(4-(4-oxo-2-phenyl-4H-chromen-6-yl)benzyl)azetidine-3-carboxylic acidYield 36%

Procedure

When the product of Step D 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 36% yield, as creamy solid. 1H-NMR (CDCl3+CD3OD) 8.31 (broad s, 1H); 7.86 (broad s, 3H); 7.77-7.52 (m, 7H); 6.69 (s, 1H); 4.21 (broad s, 2H); 4.18-4.02 (m, 4H); 3.3 (s, 1H).

Sources & evidence

ORD record
ord-8897287d465d48faa4d83b434e20267a
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

Loading…