Water → HCID 13062099, compound

HRID 223379Notes

Reaction equation

HRID 223379 reaction equation
[H-].[Li+].[C:3]([NH:9][CH2:10][C:11]1([CH2:28][CH3:29])[CH:20]2[N:15]([CH2:16][CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:19]=32)[CH2:14][CH2:13][CH2:12]1)(=O)[CH2:4][CH2:5][CH2:6][CH3:7].O.ClCCl>C(OCC)C>[CH2:3]([NH:9][CH2:10][C:11]1([CH2:28][CH3:29])[CH:20]2[N:15]([CH2:16][CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:19]=32)[CH2:14][CH2:13][CH2:12]1)[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 62714Lithium hydrideHCID 13062097HCID 13062097, compound

Product 1

HCID 13062099HCID 13062099, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a 500 ml three-necked flask of having a stirrer, a reflux condenser, a thermometer, and a dropping funnel there were placed 100 ml of anhydrous ethyl ether. When this had been cooled on an ice bath there were added 4 g of lithium hydride, and the contents of the flask were stirred for 15 minutes. There was then added very slowly a solution of 7.4 g of the product of Example 7 in 50 ml of anhydrous ethyl ether. The mixture was then heated under reflux for 2 hours and stirred for a further 15 hours at room temperature. It was then cooled on an ice bath and there were added dropwise 20 ml of water followed by 150 ml of dichloromethane. The mixture was then filtered over Celite, dried over sodium sulphate and concentrated by evaporation. There were obtained 7 g of an oil which could be crystallized to a product melting at 80° C.

Workup

  1. customIn a 500 ml three-necked flask of having
  2. customa stirrer, a reflux condenser, a thermometer, and a dropping funnel there were placed
  3. temperatureWhen this had been cooled on an ice bath
  4. temperatureThe mixture was then heated
  5. temperatureunder reflux for 2 hours
  6. stirringstirred for a further 15 hours at room temperature
  7. temperatureIt was then cooled on an ice bath
  8. filtrationThe mixture was then filtered over Celite
  9. dry with materialdried over sodium sulphate
  10. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0a6a9bcb12d143fd932290ad4e7d73f5
Source dataset
uspto-grants-1982_10
Patent number
US04353911

Reaction notes

Loading…