3-((2s)-3-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propylamino)-propionic acid methyl ester → 3-((2s)-3-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propylamino)-propionic acid

HRID 2037381Notes

Reaction equation

HRID 2037381 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][NH:6][CH2:7][C@H:8]([OH:36])[CH2:9][O:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14]([C:18]2[N:22]=[C:21]([C:23]3[CH:28]=[C:27]([CH3:29])[C:26]([CH2:30][CH:31]([CH3:33])[CH3:32])=[CH:25][N:24]=3)[O:20][N:19]=2)=[CH:13][C:12]=1[CH2:34][CH3:35]>C(O)C.[OH-].[Na+]>[CH2:34]([C:12]1[CH:13]=[C:14]([C:18]2[N:22]=[C:21]([C:23]3[CH:28]=[C:27]([CH3:29])[C:26]([CH2:30][CH:31]([CH3:33])[CH3:32])=[CH:25][N:24]=3)[O:20][N:19]=2)[CH:15]=[C:16]([CH3:17])[C:11]=1[O:10][CH2:9][C@@H:8]([OH:36])[CH2:7][NH:6][CH2:5][CH2:4][C:3]([OH:37])=[O:2])[CH3:35]

Participants

4

Reactant 1

HCID 686312243-((2s)-3-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propylamino)-propionic acid methyl ester

Product 1

HCID 442183203-((2s)-3-{2-Ethyl-4-[5-(5-isobutyl-4-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propylamino)-propionic acidYield 45.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of the compound of Example 60 (53 mg, 101 μmol) in ethanol (1 mL) and 1 M aq. NaOH (1 mL) is stirred at rt for 18 h. The ethanol is evaporated, the remaining solution is neutralized by adding 1 N aq. HCl, and the mixture is separated by prep. HPLC to give the title compound (23 mg) as a white solid; LC-MS: tR=0.88 min, [M+H]+=497.08; 1H NMR (CDCl3): δ0.98 (d, J=6.5 Hz, 6H), 1.27 (t, J=7.3 Hz, 3H), 1.93 (hept, J=7.0 Hz, 1H), 2.34 (s, 3H), 2.44 (s, 3H), 2.60 (d, J=7.3 Hz, 2H), 2.65-2.83 (m, 4H), 3.18-3.40 (m, 4H), 3.82-3.96 (m, 2H), 4.52-4.61 (m, 1H), 7.88 (s, 1H), 7.92 (s, 1H), 8.06 (s, 1H), 8.51 (s, 1H).

Workup

  1. customThe ethanol is evaporated
  2. additionby adding 1 N aq. HCl
  3. customthe mixture is separated by prep

Sources & evidence

ORD record
ord-132a91d49ac544fca5ea759910a451de
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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