Hydrochloric Acid → 3-(Isopropyl-{3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-propionic acid trifluoroacetate

HRID 2268682Notes

Reaction equation

HRID 2268682 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C[O:9][C:10](=[O:36])[CH2:11][CH2:12][N:13]([CH:33]([CH3:35])[CH3:34])[C:14](=[O:32])[C:15]1[CH:20]=[C:19]([O:21][CH2:22][CH2:23][NH:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH:18]=[C:17]([CH3:31])[CH:16]=1.[OH-].[Na+].Cl>O1CCOCC1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:33]([N:13]([C:14](=[O:32])[C:15]1[CH:20]=[C:19]([O:21][CH2:22][CH2:23][NH:24][C:25]2[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=2)[CH:18]=[C:17]([CH3:31])[CH:16]=1)[CH2:12][CH2:11][C:10]([OH:36])=[O:9])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 699474873-(Isopropyl-{3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-propionic acid methyl ester trifluoroacetate

Product 1

HCID 699505203-(Isopropyl-{3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-propionic acid trifluoroacetateYield 89.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(isopropyl-{3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-propionic acid methyl ester trifluoroacetate (0.031 g) in dioxan (1 ml) was added 2M aqueous sodium hydroxide (0.078 ml), and the resultant solution was stirred at room temperature for 3 h. 1M Aqueous hydrochloric acid (ca 0.5 ml) was added and the resultant solution was concentrated under reduced pressure. Th residue was subjected to preparative hplc and the title compound (0.027 g) was obtained as a colourless oil by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

  1. concentrationthe resultant solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a1d544d2129441c697b959e86fca9e54
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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