Chloroform → 4-(N-carbobenzyloxy-allylamino)phenylacetyl chloride
Reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C(Cl)(Cl)[Cl:16].C(=O)([O-])[O-].[Na+].[Na+].[C:25](Cl)([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>O>[C:25]([N:4]([CH2:1][CH:2]=[CH2:3])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([Cl:16])=[O:14])=[CH:9][CH:10]=1)([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26]Participants
6
Conditions
- Temperature
- 40 °C
Procedure
To 15 g. 4-(allylamino)phenylacetic acid in 200 ml. warm chloroform is added a solution of 12 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 1N hydrochloric acid, dried, and evaorated to an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. 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 ultimately to yield 4-(N-carbobenzyloxy-allylamino)phenylacetyl chloride as a viscous, orange oil.
Workup
- additionTo the vigorously stirred solution is added 10 g
- customthe layers are separated
- washwashed three times with 1N hydrochloric acid
- customdried
- dissolutionThe oil is dissolved in 300 ml
- additiontoluene, treated with 15 ml
- temperaturethionyl chloride and the solution is refluxed for 5 hours
- customThe solvents are evaporated
- dissolutionthe residue is dissolved three times in toluene
- customevaporating each time ultimately
Sources & evidence
- ORD record
- ord-4801e610fd864cbc99ef41ee1f028d61
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04281019
Reaction notes
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