Hydrochloric Acid → 3-({3-[2-(tert-Butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoyl}-phenyl-amino)-propionic acid

HRID 2268595Notes

Reaction equation

HRID 2268595 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:41])[CH2:6][CH2:7][N:8]([C:15](=[O:40])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([O:23][CH2:24][CH2:25][N:26]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>O1CCOCC1>[C:36]([O:35][C:33]([N:26]([C:27]1[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=1)[CH2:25][CH2:24][O:23][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([Cl:22])[CH:19]=1)[C:15]([N:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:7][CH2:6][C:5]([OH:41])=[O:4])=[O:40])=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 540560693-({3-[2-(tert-Butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoyl}-phenyl-amino)-propionic acid methyl ester

Product 1

HCID 183488573-({3-[2-(tert-Butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoyl}-phenyl-amino)-propionic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2M Aqueous sodium hydroxide (2.54 ml) was added to a stirred solution of 3-({3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoyl}-phenyl-amino)-propionic acid methyl ester (1.22 g) in 1,4-dioxan (15 ml). 2M Aqueous hydrochloric acid (2.54 ml) was added after 16 h. The reaction mixture was evaporated and the residue partitioned between ethyl acetate and water. The aqueous layer was removed and the organic phase was dried with brine and over sodium sulphate and then concentrated under reduced pressure to give the title compound (1.10 g) as a white foam.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe aqueous layer was removed
  4. dry with materialthe organic phase was dried with brine and over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a622c9bdce9646529c696c5bdcac71e1
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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