Hydrochloric Acid → HCID 21072918, compound

HRID 1373235Notes

Reaction equation

HRID 1373235 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:32]=[CH:33][CH:34]=1)[O:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[NH:23][CH2:24][CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])=[O:9])([CH3:6])([CH3:5])[CH3:4].O.Cl>O1CCCC1.C(O)C>[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:32]=[CH:33][CH:34]=1)[O:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[NH:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 21072934HCID 21072934, compound

Product 1

HCID 21072918HCID 21072918, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 1 N sodium hydroxide solution (15 ml, 15 mmols) was added to a solution of ethyl 4-[2-[3-(tert-butoxycarbonylaminomethyl)phenoxy]-4-chlorophenyl]aminobutyrate (4.6 g, 10 mmols) in tetrahydrofuran (15 ml) and ethanol (15 ml). The resulting mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture, which was acidified with 1 N hydrochloric acid added thereto, and then extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure to give an amorphous solid of 4-[2-[3-(tert-butoxycarbonylaminomethyl)phenoxy]-4-chlorophenyl]aminobutyric acid (4.1 g, 95%).

Workup

  1. additionadded
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e0f74c2ef6245dca529f8bb97a6b28a
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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