Hydrochloric Acid → 4-((2-Carbamoyl-phenyl)-{3-chloro-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-butyric acid

HRID 2268653Notes

Reaction equation

HRID 2268653 reaction equation
[OH-].[Na+].FC(F)(F)C(O)=O.C[O:11][C:12](=[O:45])[CH2:13][CH2:14][CH2:15][N:16]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42](=[O:44])[NH2:43])[C:17](=[O:35])[C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][NH:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[CH:21]=[C:20]([Cl:34])[CH:19]=1.Cl>O1CCOCC1>[C:42]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[N:16]([C:17](=[O:35])[C:18]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][NH:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[CH:21]=[C:20]([Cl:34])[CH:19]=1)[CH2:15][CH2:14][CH2:13][C:12]([OH:45])=[O:11])(=[O:44])[NH2:43]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 699502544-((2-Carbamoyl-phenyl)-{3-chloro-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-butyric acid methyl ester trifluoroacetate

Product 1

HCID 183491504-((2-Carbamoyl-phenyl)-{3-chloro-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-butyric acidYield 100.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2M Aqueous sodium hydroxide (0.200 ml) was added to a stirred solution of 4-((2-carbamoyl-phenyl)-{3-chloro-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoyl}-amino)-butyric acid methyl ester trifluoroacetate (0.030 g) in 1,4-dioxan (1 ml). 2M Aqueous hydrochloric acid (0.2 ml) was added after 16 h. The reaction mixture was evaporated in vacuo and the residue was subjected to preparative hplc to give the title compound (0.024 g) as a colourless gum by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

  1. customThe reaction mixture was evaporated in vacuo

Sources & evidence

ORD record
ord-840eac500fe3486089edf5c49b7e398e
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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