(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine → (S)-2-(4-Cyclohexyl-phenoxymethyl)-5-ethylsulfanylmethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237873Notes

Reaction equation

[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C@H:13]3[O:17][C:16]([NH2:18])=[N:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:23][C:24](=O)[C:25]#[C:26][CH2:27][S:28][CH2:29][CH3:30])C>C(O)(C)(C)C>[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C@H:13]3[O:17][C:16]4=[N:18][C:24](=[O:23])[CH:25]=[C:26]([CH2:27][S:28][CH2:29][CH3:30])[N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.5 g, 1.82 mmol) in t-butanol (5 mL) was added 4-ethylsulfanyl-but-2-ynoic acid ethyl ester (0.411 g, 2.39 mmol). The reaction mixture was heated in a microwave oven at 170° C. for 20 min. The solvent was removed under vacuum, and the residue purified by flash column chromatography (silica gel, MeOH/CH2Cl2) to afford 0.416 g of the title compound.

Workup

customThe solvent was removed under vacuum
customthe residue purified by flash column chromatography (silica gel, MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-ec66c336d69f4827b9e7672820b6a0e0
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642603B2

Reaction notes

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