Water → HCID 14233147, compound

HRID 1722595Notes

Reaction equation

HRID 1722595 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:20]([OH:54])[CH2:21][N:22]([C@@H:43]([CH3:53])[CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)C([C@@H]2CCCN2S(C2C=CC3C(=CC=CC=3)C=2)(=O)=O)=O)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].CO.O>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:20]([OH:54])[CH2:21][NH:22][C@@H:43]([CH3:53])[CH2:44][C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23689386Potassium hydroxide methanolHCID 70380686HCID 70380686, compound

Product 1

HCID 14233147HCID 14233147, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.61 g of 8-benzyloxy-5-{(1S)-1-hydroxy-2-[N-((1S)-2-(p-methoxyphenyl)-1-methylethyl)-N-((2S)-1-(2-naphthylsulfonyl)-pyrrolidine-2-carbonyl)amino]ethyl}carbostyril are dissolved in 100 ml of methanol, and 35 ml of 1N potassium hydroxide-methanol and 10 ml of water are added thereto. The mixture is refluxed for 3 hours with stirring. The mixture is concentrated under reduced pressure to remove solvent. The residue is extracted with chloroform, and the extract is dried and concentrated under reduced pressure to remove solvent. The residue is recrystallized twice from ethyl acetate. 1.1 g of 8-benzyloxy-5-{(1S)-1-hydroxy-2-[N-((1S)-2-(p-methoxyphenyl)-1-methylethyl)amino]ethyl}carbostyril are obtained as colorless needles. Yield: 68.8%.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove solvent
  4. extractionThe residue is extracted with chloroform
  5. customthe extract is dried
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. customThe residue is recrystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-7e0ab78544234808b9fe8231a9f72363
Source dataset
uspto-grants-1989_08
Patent number
USRE033024

Reaction notes

Loading…