2-Propynoic acid, 3-cyclopentyl-, ethyl ester → (S)-2-(4-Bicyclo[3.3.1]non-9-yl-phenoxymethyl)-5-cyclopentyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7one

HRID 237856Notes

Reaction equation

HRID 237856 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.C([O:26][C:27](=O)[C:28]#[C:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)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:27](=[O:26])[CH:28]=[C:29]([CH:30]6[CH2:34][CH2:33][CH2:32][CH2:31]6)[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 123838592-Propynoic acid, 3-cyclopentyl-, ethyl esterHCID 68527534(S)-5-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 25069828(S)-2-(4-Bicyclo[3.3.1]non-9-yl-phenoxymethyl)-5-cyclopentyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7one

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 cyclopentyl-propynoic acid ethyl ester (see Example 102) employing the procedure described in Example 95. [α]D25 −4.80 (c 0.5, CHCl3).

Sources & evidence

ORD record
ord-04a0c205cd034810a1a970f0b9338989
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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