Lithium Hydroxide → HCID 91885612, compound

HRID 59912Notes

Reaction equation

HRID 59912 reaction equation
[CH2:1]([O:3][C:4]1[CH:37]=[CH:36][CH:35]=[CH:34][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19]([NH:21][C@@H:22]([C:24]3[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=3)[C:27]([O:29]C)=[O:28])[CH3:23])=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2].[Li+].[OH-]>>[CH2:1]([O:3][C:4]1[CH:37]=[CH:36][CH:35]=[CH:34][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:14]=[CH:15][C:16]([C:19]([NH:21][C@@H:22]([C:24]3[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=3)[C:27]([OH:29])=[O:28])[CH3:23])=[O:20])=[CH:17][N:18]=2)[CH2:8]1)[CH3:2]

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 118366227methyl 3-((R)-1-(2-((R)-3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)ethyl)benzoate

Product 1

HCID 91885612HCID 91885612, compound

Procedure

3-((R)-1-(2-((R)-3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)ethyl)benzoic acid was prepared from methyl 3-((R)-1-(2-((R)-3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)ethyl)benzoate using Ester Hydrolysis Method 1 (LiOH). 1H NMR (400 MHz, DMSO-d6) δ 12.9 (br s, 1H), 8.76 (s, 2H), 8.70 (d, 1H), 7.96 (s, 1H), 7.81 (d, 1H), 7.61 (d, 1H), 7.45 (dd, 1H), 7.03 (d, 1H), 6.89 (m, 3H), 5.18 (m, 1H), 4.30 (m, 1H), 4.19 (dd, 1H), 3.89 (m, 4H), 3.77 (m, 1H), 2.01 (m, 1H), 1.83 (m, 2H), 1.51 (m, 1H), 1.46 (d, 3H), 1.21 (t, 3H). MS (ES+) 491 (M+H).

Sources & evidence

ORD record
ord-61f510d0b86247eaaaa1ae15c049bba3
Source dataset
uspto-grants-2016_09
Patent number
US09440949B2

Reaction notes

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