Potassium Carbonate → N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(oxazol-5-yl)phenethoxy)propanamide

HRID 909908Notes

Reaction equation

[CH:1]1([N:7]([CH2:23][CH:24]([O:27][CH3:28])[O:25][CH3:26])[C:8](=[O:22])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[O:21])[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C(S([CH2:38][N+:39]#[C-:40])(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([N:7]([CH2:23][CH:24]([O:27][CH3:28])[O:25][CH3:26])[C:8](=[O:22])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[O:21][CH:40]=[N:39][CH:38]=3)[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To N-cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-formylphenethoxy)propanamide [Example 10, Step ii)] (600 mg) in a 10 ml microwave vial was added toluenesulfonylmethyl isocyanide (329 mg), potassium carbonate (233 mg) and methanol (2 mL). The vial was sealed and heated at 80° C. for 40 min within a microwave before cooling to room temperature. The solvents were evaporated under vacuum followed by the addition of water, which was extracted once with ethyl acetate. The organic phase was washed once with water, dried over sodium sulphate, filtered and the solvent removed to afford desired material, which was carried onto the next step directly. MS [M+H-MeOH]+=399 (MultiMode+)

Workup

customThe vial was sealed
temperaturebefore cooling to room temperature
customThe solvents were evaporated under vacuum
additionfollowed by the addition of water, which
extractionwas extracted once with ethyl acetate
washThe organic phase was washed once with water
dry with materialdried over sodium sulphate
filtrationfiltered
customthe solvent removed
customto afford desired material, which

Sources & evidence

ORD record: ord-fa6f00f8c2134d03a0deeae3bea3d519
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017602B2

Reaction notes

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