Sodium Hydroxide → 5-carboxymethyl-3-(1-carboxynonylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1719128Notes

Reaction equation

HRID 1719128 reaction equation
[C:1]([CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][CH2:8][CH:7]([NH:16][CH:17]([C:26]([O:28]CC)=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:6]1=[O:31])([OH:3])=[O:2].[OH-].[Na+]>C(O)C>[C:1]([CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[S:9][CH2:8][CH:7]([NH:16][CH:17]([C:26]([OH:28])=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:6]1=[O:31])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 134545685-carboxymethyl-3-(1-ethoxycarbonylnonylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 202675715-carboxymethyl-3-(1-carboxynonylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 92.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

690 mg of the 5-carboxymethyl-3-(1-ethoxycarbonylnonylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one obtained in Example 18 was dissolved in 10 ml of ethanol and 4 ml of a 1N aqueous solution of sodium hydroxide and then reacted at room temperature for 3 hours. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in 5 ml of water. This solution was adjusted to pH 2 with hydrochloric acid. The precipitated white crystals were separated by filtration and washed thoroughly with water to obtain 600 mg of the desired compound.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in 5 ml of water
  3. customThe precipitated white crystals were separated by filtration
  4. washwashed thoroughly with water

Sources & evidence

ORD record
ord-aae37895bee047ddbab6ed68a32fec08
Source dataset
uspto-grants-1985_09
Patent number
US04539150

Reaction notes

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