Toluene → 8-[[2-(Chloromethyl)-4-methyl-1-oxopentyl]amino]octanoic acid

HRID 225106

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

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-5b7717d8116b45ec806aa6dd8478d922
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04235885

Linked notes

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