HCID 22975755, compound → HCID 23435763, compound

HRID 2120966Notes

Reaction equation

HRID 2120966 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][C:12]3([CH2:19][CH2:18][CH:17]([CH2:20][C:21]([O:23]CC)=[O:22])[CH2:16][CH2:15]3)[CH2:11][CH2:10]2)=[CH:3][CH:2]=1>C(O)C.[OH-].[Na+].O>[N:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][C:12]3([CH2:19][CH2:18][CH:17]([CH2:20][C:21]([OH:23])=[O:22])[CH2:16][CH2:15]3)[CH2:13][CH2:14]2)=[CH:5][CH:6]=1

Participants

5

Reactant 1

HCID 22975755HCID 22975755, compound

Product 1

HCID 23435763HCID 23435763, compound

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 0.05 g (0.145 mmol) of the ester from Example 22 in 2 ml ethanol were added three drops of 2N aqueous sodium hydroxide solution. The mixture was heated at 70° C. for 3 h and diluted with 10 ml water. It was washed two times with dichloromethane, and the aqueous layer was adjusted to pH 7-8 with hydrochloric acid. After another extraction with dichloromethane the aqueous layer was concentrated under reduced pressure and the residue stirred with 20 ml of a mixture of ethanol/dichloromethane 9:1. Solids were removed by filtration, and the filtrate was concentrated in vacuo to leave the pure title acid.

Workup

  1. washIt was washed two times with dichloromethane
  2. extractionAfter another extraction with dichloromethane the aqueous layer
  3. concentrationwas concentrated under reduced pressure
  4. customSolids were removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-901a8de3dcc84bdc96d755382e37b781
Source dataset
uspto-grants-2004_02
Patent number
US06693109B2

Reaction notes

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