Hydrochloric Acid → HCID 178427483, compound

HRID 1976300Notes

Reaction equation

HRID 1976300 reaction equation
C([O:3][C:4]([CH2:6][C:7]1([CH3:32])[CH2:16][CH2:15][C:14]2[C:9](=[C:10]([CH3:31])[C:11]([CH3:30])=[C:12]([S:18]([NH:21][C:22](=[NH:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:20])=[O:19])[C:13]=2[CH3:17])[O:8]1)=[O:5])C.CCOC(C)=O.Cl>C(O)C.[OH-].[Na+]>[C:4]([CH2:6][C:7]1([CH3:32])[CH2:16][CH2:15][C:14]2[C:9](=[C:10]([CH3:31])[C:11]([CH3:30])=[C:12]([S:18]([NH:21][C:22](=[NH:29])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)(=[O:19])=[O:20])[C:13]=2[CH3:17])[O:8]1)([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178470658HCID 178470658, compound

Product 1

HCID 178427483HCID 178427483, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-(2-ethoxycarbonylmethyl-2,5,7,8-tetramethylchroman-6-sulfonyl)benzamidine (1.54 g) in a mixture of ethanol (EtOH) (30 ml) and 1N NaOH (7.05 ml) was stirred at room temperature for 30 hours. EtOH was evaporated under reduced pressure to give a residue. A mixture of AcOEt and 1N HCl was added to the residue. The organic phase was washed with water and brine, and dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure to give N-(2-carboxymethyl-2,5,7,8-tetramethylchroman-6-sulfonyl)benzamidine as a glass (1.49 g).

Workup

  1. customEtOH was evaporated under reduced pressure
  2. customto give a residue
  3. additionwas added to the residue
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e76f4aeb82c4482082a3b89460eb20a9
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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