Ethyl hept-2-ynoate → (S)-5-n-Butyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237837Notes

Reaction equation

HRID 237837 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][CH2:28][CH2:29][CH3:30])C>CS(C)=O>[CH2:27]([C:26]1[N:15]2[CH2:14][C@@H:13]([CH2:12][O:11][C:10]3[CH:19]=[CH:20][C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:8][CH:9]=3)[O:17][C:16]2=[N:18][C:24](=[O:23])[CH:25]=1)[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 85647Ethyl hept-2-ynoateHCID 66875140(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 25071430(S)-5-n-Butyl-2-(4-cyclohexyl-phenoxymethyl)-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared from (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine and hept-2-ynoic acid ethyl ester employing the procedure described in Example 99. [α]D25 +8.40 (c 0.5, DMSO)

Sources & evidence

ORD record
ord-6314ad170c68471b841e886fb01255b6
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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