(S)-3-Ethyl-4-[2-hydroxy-3-(2-hydroxy-acetylamino)-propoxy]-5-methyl-benzoic acid → N-((2S)-3-{2-Ethyl-4-[3-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-5-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 2037385Notes

Reaction equation

HRID 2037385 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:7][N:6]=1)=[NH:4].[CH2:16]([C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([CH3:37])[C:26]=1[O:27][CH2:28][C@@H:29]([OH:36])[CH2:30][NH:31][C:32](=[O:35])[CH2:33][OH:34])[C:21](O)=O)[CH3:17]>>[CH2:16]([C:18]1[CH:19]=[C:20]([C:21]2[O:1][N:2]=[C:3]([C:5]3[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:7][N:6]=3)[N:4]=2)[CH:24]=[C:25]([CH3:37])[C:26]=1[O:27][CH2:28][C@@H:29]([OH:36])[CH2:30][NH:31][C:32](=[O:35])[CH2:33][OH:34])[CH3:17]

Participants

3

Reactant 2

HCID 66931956(S)-3-Ethyl-4-[2-hydroxy-3-(2-hydroxy-acetylamino)-propoxy]-5-methyl-benzoic acidHCID 178426677HCID 178426677, compound

Product 1

HCID 44218483N-((2S)-3-{2-Ethyl-4-[3-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-5-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamideYield 34.4%

Procedure

The title compound (32 mg) is prepared by coupling and cyclizing N-hydroxy-5-isobutyl-4-methyl-pyridine-2-carboxamidine (40 mg, 193 μmol) with 3-ethyl-4-[(S)-2-hydroxy-3-(2-hydroxy-acetylamino)-propoxy]-5-methyl-benzoic acid (60 mg, 193 μmol) as described in Example 1; LC-MS: tR=0.95 min, [M+H]+=482.86.

Sources & evidence

ORD record
ord-db3ea2489e294c8d8afae4960bb78b3c
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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