Hydrochloric Acid → HCID 21073055, compound

HRID 1373212Notes

Reaction equation

HRID 1373212 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:41]=[CH:42][CH:43]=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]([OH:40])=[CH:36][CH:35]=1)[C:24](=[O:32])[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:41]=[CH:42][CH:43]=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:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=1)[C:24](=[O:32])[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 21072946HCID 21072946, compound

Product 1

HCID 21073055HCID 21073055, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 1 N sodium hydroxide solution (8 ml, 8 mmols) was added to a solution of ethyl N-[2-[3-(tert-butoxycarbonylaminomethyl)phenoxy]-4-chlorophenyl]-N-(4-hydroxybenzyl)succinamate (2.57 g, 4 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 then acidified with 1 N hydrochloric acid added thereto. Then, this was 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-(4-hydroxybenzyl) succinamic acid (1.47 g, 99%).

Workup

  1. additionadded
  2. extractionThen, this was extracted 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-4dc680412d8647afb17a6f6ffc565575
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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