Hydrochloric Acid → 3-[(3-Chloro-5-methoxy-benzoyl)-isopropyl-amino]-propionic acid

HRID 2268598Notes

Reaction equation

HRID 2268598 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:23])[CH2:6][CH2:7][N:8]([C:12](=[O:22])[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([Cl:21])[CH:14]=1)[CH:9]([CH3:11])[CH3:10].Cl>O1CCOCC1>[Cl:21][C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([O:19][CH3:20])[CH:16]=1)[C:12]([N:8]([CH:9]([CH3:11])[CH3:10])[CH2:7][CH2:6][C:5]([OH:23])=[O:4])=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 699488253-[(3-Chloro-5-methoxy-benzoyl)-isopropyl-amino]-propionic acid methyl ester

Product 1

HCID 183491943-[(3-Chloro-5-methoxy-benzoyl)-isopropyl-amino]-propionic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2M Aqueous sodium hydroxide (4.5 ml) was added to a stirred solution of 3-[(3-chloro-5-methoxy-benzoyl)-isopropyl-amino]-propionic acid methyl ester (1.50 g) in 1,4-dioxan (30 ml). 2M aqueous hydrochloric acid (4.5 ml) was added after 20 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 (1.41 g) as a brown solid.

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-f187a4aeeef14e0fa5b0e1a7aef3c590
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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