Toluene → 8-[[2-(Chloromethyl)-4-methyl-1-oxopentyl]amino]octanoic acid
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].C1(C)C=CC=CC=1.[Cl:19][CH2:20][CH:21]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22](Cl)=[O:23]>O.[OH-].[Na+].C1COCC1>[Cl:19][CH2:20][CH:21]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 5 °C
Procedure
8-Amino caprylic acid (4.3 g) is dissolved in 20 ml of water containing 1.1 g of sodium hydroxide. To this is added 20 ml of THF, and 5 ml of toluene, and the solution is cooled to 5° C. 2-(Chloromethyl)-4-methylvaleryl chloride is dissolved in 10 ml of THF and added dropwise to the above solution. The pH of the reaction mixture is maintained between 8 and 9 during the reaction time by the addition of a total of 1.1 g of sodium hydroxide in 20 ml of water, as needed. After stirring at room temperature for about 16 hours, the aqueous layer is separated and acidified with 10% hydrochloric acid. Product is extracted with ethyl acetate and the ethyl acetate is dried with magnesium sulfate, filtered and concentrated in vacuo to yield 5.6 g of product.
Workup
- additionadded dropwise to the above solution
- customthe aqueous layer is separated
- extractionProduct is extracted with ethyl acetate
- dry with materialthe ethyl acetate is dried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-f2c5031f1a974f85bd9c2e1770b3a975
- Source dataset
- uspto-grants-1981_10
- Patent number
- US04297275
Reaction notes
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