(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine → (S)-2-(4-Cyclohexyl-phenoxymethyl)-5-(1-fluoro-1-methyl-ethyl)-2,3-dihydro-oxazolo-[3,2-a]pyrimidin-7-one

HRID 237850Notes

Reaction equation

HRID 237850 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][C:27]([F:30])([CH3:29])[CH3:28])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:24](=[O:23])[CH:25]=[C:26]([C:27]([F:30])([CH3:29])[CH3:28])[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 66875140(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamineHCID 866170244-Fluoro-4-methyl-pent-2-ynoic acid ethyl ester

Product 1

HCID 25071434(S)-2-(4-Cyclohexyl-phenoxymethyl)-5-(1-fluoro-1-methyl-ethyl)-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-fluoro-4-methyl-pent-2-ynoic acid ethyl ester employing the procedure described in Example 105. [α]D25 −21.61 (c 0.56, CHCl3).

Sources & evidence

ORD record
ord-3594216d10334088bac67f19e71891de
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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