Hydrochloric Acid → 2-(Tert-butyl(hex-5-ynyl)amino)-2-oxoacetic acid

HRID 1971732Notes

Reaction equation

[C:1]([N:5]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])[C:6](=[O:12])[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>O1CCOCC1.O>[C:1]([N:5]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])[C:6](=[O:12])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 0.7 g of 17d in 8 ml of dioxane was mixed with a solution of 0.3 g of KOH in 3 ml of water. The mixture was stirred for 2 h at 50° C. and then diluted with 30 ml of water and acidified to pH3 with 0.5 N HCl. The product was extracted with ethyl acetate. The extract was washed with water, dried and concentrated, to give 0.50 g of 19a as a colorless oil. NMR (CDCl3) δ 1.53 (s and m, 11, tertC4H9 and CH2), 1.78 (m, 2, CH2), 1.97 (t, 1, acetylene), 2.20 (m, 2, CH2), 3.56 (m, 2, CH2).

Workup

extractionThe product was extracted with ethyl acetate
washThe extract was washed with water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-3d10eeb7b7ad4f7bb4577dd8e992ae6f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431564B2

Reaction notes

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