Chloroform → N-carbobenzyloxy-4-(15-carbomethoxypentadecylamino)benzoyl chloride
Reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=1)([O:3][CH3:4])=[O:2].C(Cl)(Cl)[Cl:31].C(=O)([O-])[O-].[Na+].[Na+].[C:40](Cl)([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41]>O>[C:40]([N:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:1]([O:3][CH3:4])=[O:2])[C:21]1[CH:22]=[CH:23][C:24]([C:25]([Cl:31])=[O:27])=[CH:28][CH:29]=1)([O:42][CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)=[O:41]Participants
6
Conditions
- Temperature
- 40 °C
Procedure
To 15 g. of 4-(15-carbomethoxypentadecylamino)benzoic acid in 200 ml. warm chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously stirred solution is added 10 g. carbobenzyloxy chloride. After 2 hours stirring at 40° C., the layers are separated, washed three times with 1 N hydrochloric acid, dried, and evaporated to an oil. The oil is disolved in 300 ml. toluene, treated with 15 ml. of thionyl chloride, and the solution is refluxed for 5 hours. The solvents are evaporated and the residue is dissolved three times in toluene, evaporating each time to yield a viscous, orange oil.
Workup
- additionTo the vigorously stirred solution is added 10 g
- customthe layers are separated
- washwashed three times with 1 N hydrochloric acid
- customdried
- customevaporated to an oil
- additiontoluene, treated with 15 ml
- temperatureof thionyl chloride, and the solution is refluxed for 5 hours
- customThe solvents are evaporated
- dissolutionthe residue is dissolved three times in toluene
- customevaporating each time
- customto yield a viscous, orange oil
Sources & evidence
- ORD record
- ord-96c10fa938d84b7395c765631caacf61
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04281018
Reaction notes
Loading…