Hydrochloric Acid → HCID 21073053, compound

HRID 1373216Notes

Reaction equation

HRID 1373216 reaction equation
[OH-:1].[Na+].[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:42]=[CH:43][CH:44]=1)[O:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N:23]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[C:35]=1Cl)C(=O)CCC(OCC)=O)=[O:9])([CH3:6])([CH3:5])[CH3:4].[OH2:45].[ClH:46].[O:47]1[CH2:51][CH2:50][CH2:49][CH2:48]1>C(O)C>[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:42]=[CH:43][CH:44]=1)[O:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N:23]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([Cl:46])=[C:36]([Cl:40])[CH:35]=1)[C:51](=[O:47])[CH2:50][CH2:49][C:48]([OH:45])=[O:1])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21072944HCID 21072944, compound

Product 1

HCID 21073053HCID 21073053, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous 1 N sodium hydroxide solution (10 ml, 10 mmols) was added to a solution of ethyl N-[2-[3-(tert-butoxycarbonylaminomethyl)phenoxy]-4-chlorophenyl]-N-(2,3-dichlorobenzyl)succinamate (3.18 g, 5 mmols) in tetrahydrofuran (10 ml) and ethanol (10 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 N-[2-[3-(tert-butoxycarbonylaminomethyl)phenoxy]-4-chlorophenyl]-N-(3,4-dichlorobenzyl) succinamic acid (2.46 g, 81.2%).

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-d950b8c32eab4d28b712b5fa7af40935
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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