Triethylamine → HCID 15571067, compound

HRID 2286245Notes

Reaction equation

[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]([OH:9])=O)(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[CH3:27][O:28][CH:29]([O:32][CH3:33])[CH2:30][NH2:31]>O1CCCC1>[CH3:27][O:28][CH:29]([O:32][CH3:33])[CH2:30][NH:31][C:7](=[O:9])[CH:6]([CH2:5][S:4][C:1](=[O:3])[CH3:2])[CH2:10][CH:11]([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -5 °C

Procedure

A solution of 2-[(acetylthio)methyl]-4-methylpentanoic acid (2.0 g) and triethyl amine (1.0 g) in 50 ml of tetrahydrofuran (THF) is cooled to -5° C. Ethyl chloroformate (1.1 g) in 5 ml of THF is added dropwise and the reaction mixture is stirred at -5° C. for 30 minutes. Amino acetaldehyde dimethyl acetal (1.1 g) in 20 ml of THF is added dropwise to the mixed anhydride solution at -5° C. After addition, it is stirred at 10°-20° C. for 2 hours and stored at 0° C. for about 16 hours. Triethylamine hydrochloride is filtered off and the filtrate is concentrated in vacuo. The residue (2.1 g) is dissolved in 3 ml of ether. Silica gel (5 g) is added and ether is evaporated off. This is placed on top of 40 g of dry silica gel and washed through with pentane, 1:1 pentane:ether and finally ether. Product elutes with ether to yield 1.3 g of product which solidifies to give a low melting waxy solid.

Workup

additionAfter addition, it
stirringis stirred at 10°-20° C. for 2 hours
waitstored at 0° C. for about 16 hours
filtrationTriethylamine hydrochloride is filtered off
concentrationthe filtrate is concentrated in vacuo
dissolutionThe residue (2.1 g) is dissolved in 3 ml of ether
additionSilica gel (5 g) is added
customether is evaporated off
washwashed through with pentane, 1:1 pentane

Sources & evidence

ORD record: ord-914c785390b243b6b54fe0d4bc3e31af
Source dataset: uspto-grants-1982_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04327111

Reaction notes

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