Ethyl 4-methoxybut-2-ynoate → (S)-2-(4-Cyclohexyl-phenoxymethyl)-5-methoxymethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237843Notes

Reaction equation

HRID 237843 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.[CH2:21]([O:23][C:24](=O)[C:25]#[C:26][CH2:27][O:28]C)C>C(Cl)(Cl)Cl>[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:27](=[O:28])[CH:26]=[C:25]([CH2:24][O:23][CH3:21])[N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 23249615Ethyl 4-methoxybut-2-ynoateHCID 66875140(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 25071734(S)-2-(4-Cyclohexyl-phenoxymethyl)-5-methoxymethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared from (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine and 4-methoxy-but-2-ynoic acid ethyl ester (Larock, J Org Chem 2002, 67, 9318) employing the procedure described in Example 105. [α]D25 −17.80 (c 0.5, CHCl3).

Sources & evidence

ORD record
ord-53ab9607b5c940769ebcf82b5d28847a
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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