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HCID 22975755, compound → HCID 23435763, compound

HRID 1596686
Notes
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Reaction equation

HRID 1596686 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-8f9d6448796643eeb0093073363a1c92
Source dataset
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06291469B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes