Acetic Acid → HCID 70069849, compound

HRID 1638992Notes

Reaction equation

HRID 1638992 reaction equation
C([O:3][C:4]([C@@H:6]([NH:17][CH:18]1[CH2:24][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[N:20]([CH2:29][C:30]([O:32]CC)=[O:31])[C:19]1=[O:35])[CH2:7][S:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:5])C.[OH-].[Na+].CO.C(O)(=O)C>O>[OH2:3].[C:4]([C@@H:6]([NH:17][CH:18]1[CH2:24][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[N:20]([CH2:29][C:30]([OH:32])=[O:31])[C:19]1=[O:35])[CH2:7][S:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([OH:5])=[O:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 14675937HCID 14675937, compound

Product 1

HCID 70069849HCID 70069849, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.5 g of dihydrobromide of the A-isomer of ethyl 3-[1(R)-ethoxycarbonyl-2-{2-(4-piperidyl)ethylthio}ethyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetate obtained in Example 4 is dissolved in 10 ml of water. The resulting aqueous solution is added dropwise to 18 ml of an aqueous solution of 2N sodium hydroxide. After stirring for 1 hour at room temperature, 6 ml of methanol is added, and the system further stirred for 1 hour. After neutralizing the reaction liquid with 7.2 ml of acetic acid, the solvent is distilled off under reduced pressure. After concentration, the residue is purified by HP-20 column chromatography (water:methanol=3:1). The effluent is concentrated under reduced pressure, and the resulting residue is recrystallized from 5 ml of water to give 324 mg of the A isomer of 3-[1(R)-carboxy-2-{2-(4-piperidyl)ethylthio}ethyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetic acid monohydrate as a colorless powder.

Workup

  1. stirringthe system further stirred for 1 hour
  2. distillationthe solvent is distilled off under reduced pressure
  3. concentrationAfter concentration
  4. customthe residue is purified by HP-20 column chromatography (water:methanol=3:1)
  5. concentrationThe effluent is concentrated under reduced pressure
  6. customthe resulting residue is recrystallized from 5 ml of water

Sources & evidence

ORD record
ord-46885f43d9fd4598963f32a0c0c59450
Source dataset
uspto-grants-1989_11
Patent number
US04882326

Reaction notes

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