Ethyl 4-methoxybut-2-ynoate → (S)-2-(4-Bicyclo[3.3.1]non-9-yl-phenoxymethyl)-5-methoxymethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237853Notes

Reaction equation

HRID 237853 reaction equation
[CH:1]12[CH:9]([C:10]3[CH:23]=[CH:22][C:13]([O:14][CH2:15][C@H:16]4[O:20][C:19]([NH2:21])=[N:18][CH2:17]4)=[CH:12][CH:11]=3)[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2.[CH2:24]([O:26][C:27](=O)[C:28]#[C:29][CH2:30][O:31]C)C>C(Cl)(Cl)Cl>[CH:1]12[CH:9]([C:10]3[CH:23]=[CH:22][C:13]([O:14][CH2:15][C@H:16]4[O:20][C:19]5=[N:21][C:30](=[O:31])[CH:29]=[C:28]([CH2:27][O:26][CH3:24])[N:18]5[CH2:17]4)=[CH:12][CH:11]=3)[CH:5]([CH2:4][CH2:3][CH2:2]1)[CH2:6][CH2:7][CH2:8]2

Participants

4

Reactant 2

HCID 23249615Ethyl 4-methoxybut-2-ynoateHCID 68527534(S)-5-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 25069825(S)-2-(4-Bicyclo[3.3.1]non-9-yl-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-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (see Example 20) and 4-methoxy-but-2-ynoic acid ethyl ester (see Example 106) employing the procedure described in Example 95. [α]D25 −14.55 (c 0.495, CHCl3).

Sources & evidence

ORD record
ord-daacd1db593242bfa705f48feac2e4e0
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

Loading…