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

HRID 1719118Notes

Reaction equation

HRID 1719118 reaction equation
C([O:3][C:4]([CH:6]([NH:15][CH:16]1[C:22](=[O:23])[N:21]([CH2:24][C:25]([O:27]CC)=[O:26])[C:20]2[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=2[S:18][CH2:17]1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([CH:6]([NH:15][CH:16]1[C:22](=[O:23])[N:21]([CH2:24][C:25]([OH:27])=[O:26])[C:20]2[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=2[S:18][CH2:17]1)[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 134744743-(1-ethoxycarbonyl-3-phenylpropylamino)-5-ethoxycarbonylmethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 133751243-(1-carboxy-3-phenylpropylamino)-5-carboxymethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 61.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.2 g of 3-(1-ethoxycarbonyl-3-phenylpropylamino)-5-ethoxycarbonylmethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one was dissolved in 15 ml of ethanol, and 6 ml of 1N NaOH was added thereto. The resulting mixture was stirred at room temperature, so that white crystals were precipitated. After 1.5 hours, the ethanol was distilled off under reduced pressure and water was added to the residue. After a small amount of insoluble matter was filtered off, the filtrate was adjusted to pH 3-4 with 6N hydrochloric acid. The precipitated crystals were separated by filtration and washed with cold water and then with ether to obtain 650 mg of the desired compound.

Workup

  1. customwere precipitated
  2. distillationthe ethanol was distilled off under reduced pressure and water
  3. additionwas added to the residue
  4. filtrationAfter a small amount of insoluble matter was filtered off
  5. customThe precipitated crystals were separated by filtration
  6. washwashed with cold water

Sources & evidence

ORD record
ord-f353b51500464d3a944c722b68f26198
Source dataset
uspto-grants-1985_09
Patent number
US04539150

Reaction notes

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