Hydrochloric Acid → 5-carboxymethyl-3-(1-carboxyethylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride

HRID 1719123Notes

Reaction equation

HRID 1719123 reaction equation
[ClH:1].[C:2]([CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][CH2:9][CH:8]([NH:17][CH:18]([C:20]([O:22]CC)=[O:21])[CH3:19])[C:7]1=[O:25])([OH:4])=[O:3].[OH-].[Na+].Cl>O>[ClH:1].[C:2]([CH2:5][N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][CH2:9][CH:8]([NH:17][CH:18]([C:20]([OH:22])=[O:21])[CH3:19])[C:7]1=[O:25])([OH:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 202675625-carboxymethyl-3-(1-ethoxycarbonylethylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride

Product 1

HCID 202675665-carboxymethyl-3-(1-carboxyethylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochlorideYield 80.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 mg of the 5-carboxymethyl-3-(1-ethoxycarbonylethylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride obtained in Example 12 was dissolved in 5 ml of water and 1.5 ml of a 1N aqueous solution of sodium hydroxide and then reacted at room temperature for an hour. Thereafter, the solution was adjusted to pH 1-2 with hydrochloric acid and concentrated to dryness under reduced pressure. Ethanol was added to the residue and the insoluble matter was removed by filtration. After the filtrate was concentrated, ether was added thereto so as to cause crystallization. Thus, there was obtained 150 mg of the desired compound.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. additionEthanol was added to the residue
  3. customthe insoluble matter was removed by filtration
  4. concentrationAfter the filtrate was concentrated
  5. additionether was added
  6. customcrystallization

Sources & evidence

ORD record
ord-55866d997cdc4868b302f4ceda6beb42
Source dataset
uspto-grants-1985_09
Patent number
US04539150

Reaction notes

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