4-benzyloxy-N-[2,2-diethoxy-2-(2-isobutyl-6-methyl-pyridin-4-yl)-ethyl]-3-ethyl-5-methyl-benzamide → 4-benzyloxy-3-ethyl-N-[2-(2-isobutyl-6-methyl-pyridin-4-yl)-2-oxo-ethyl]-5-methyl-benzamide

HRID 2040831Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:36]([CH3:37])=[CH:35][C:12]([C:13]([NH:15][CH2:16][C:17](OCC)([O:29]CC)[C:18]2[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH:19]=2)=[O:14])=[CH:11][C:10]=1[CH2:38][CH3:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(C)=O.Cl>[CH2:1]([O:8][C:9]1[C:36]([CH3:37])=[CH:35][C:12]([C:13]([NH:15][CH2:16][C:17]([C:18]2[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH:19]=2)=[O:29])=[O:14])=[CH:11][C:10]=1[CH2:38][CH3:39])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of the above 4-benzyloxy-N-[2,2-diethoxy-2-(2-isobutyl-6-methyl-pyridin-4-yl)-ethyl]-3-ethyl-5-methyl-benzamide (112 mg, 0.210 mmol) in acetone (5 mL), 1 N aq. HCl (5.5 mL) is added and the mixture is stirred at 70° C. for 5 h. The acetone is evaporated and the remaining mixture is cooled to 0° C. before it is neutralized with aq. NaOH solution and extracted twice with EA (2×20 mL). The combined org. extracts are dried over Na2SO4, filtered and concentrated. The crude product is purified by prep. TLC using heptane:EA 1:2 to give 4-benzyloxy-3-ethyl-N-[2-(2-isobutyl-6-methyl-pyridin-4-yl)-2-oxo-ethyl]-5-methyl-benzamide (35 mg) as a yellow wax; LC-MS: tR=1.03*, [M+1]+=458.91.

Workup

customThe acetone is evaporated
temperaturethe remaining mixture is cooled to 0° C. before it
extractionextracted twice with EA (2×20 mL)
dry with materialextracts are dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product is purified by prep

Sources & evidence

ORD record: ord-f9d6f53829db4f2cbd19cfedf06d0426
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580824B2

Reaction notes

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