Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate → 1-(4-(3-(1-Admantanyl)-4-methoxybenzyloxy)benzyl)azetidine-3-carboxylic acid

HRID 717679Notes

Reaction equation

HRID 717679 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:31]=[CH:32][C:33]=3[O:34][CH3:35])[CH2:14][O:15][C:16]3[CH:30]=[CH:29][C:19]([CH2:20][N:21]4[CH2:24][CH:23]([C:25]([O:27]C)=[O:26])[CH2:22]4)=[CH:18][CH:17]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.COC(C1CN(CC2C=CC(OCC3C4C=C(Cl)C=CC=4OC=3)=CC=2)C1)=O>>[C:1]12([C:11]3[CH:12]=[C:13]([CH:31]=[CH:32][C:33]=3[O:34][CH3:35])[CH2:14][O:15][C:16]3[CH:30]=[CH:29][C:19]([CH2:20][N:21]4[CH2:22][CH:23]([C:25]([OH:27])=[O:26])[CH2:24]4)=[CH:18][CH:17]=3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

3

Reactant 2

HCID 66614996Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylateHCID 66615154Methyl 1-(4-(3-(1-admantanyl)-4-methoxybenzyloxy)benzyl)azetidine-3-carboxylate

Product 1

HCID 462004531-(4-(3-(1-Admantanyl)-4-methoxybenzyloxy)benzyl)azetidine-3-carboxylic acidYield 61%

Procedure

When the product of Step C was substituted for methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate in Example 25, Step E, the similar procedure afforded the title compound in 61% yield, as creamy solid. 1H-NMR (CDCl3:CD3OD) 7.33 (d, 2H, J=8.59 Hz); 7.17-7.12 (m, 2H); 6.92 (d, 2H, J=8.64 Hz); 6.79 (d, 1H, J=8.21 Hz); 4.87 (s, 2H); 4.13 (s, 2H); 4.08-4.02 (m, 4H); 2.0 (s, 6H); 1.97 (s, 3H); 1.68 (s, 6H).

Sources & evidence

ORD record
ord-56ccee11cd9446f48bc888f1900e0f21
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

Loading…