(-)-Epichlorohydrin → (S)-5-Fluoromethyl-2-[4-(3,3,5,5-tetramethyl-cyclohexyl)-phenoxymethyl]-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237852Notes

Reaction equation

HRID 237852 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([C:10]2[CH:23]=[CH:22][C:13]([O:14][CH2:15][CH:16]3[O:20][C:19]([NH2:21])=[N:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:3]1.CC1(C)CC(C)(C)CC(C2C=CC(O)=CC=2)C1.C([C@@H]1OC1)Cl.C([O:49][C:50](=O)[C:51]#[C:52][CH2:53][F:54])C>C(Cl)(Cl)Cl>[F:54][CH2:53][C:52]1[N:18]2[CH2:17][C@@H:16]([CH2:15][O:14][C:13]3[CH:12]=[CH:11][C:10]([CH:4]4[CH2:5][C:6]([CH3:8])([CH3:9])[CH2:7][C:2]([CH3:24])([CH3:1])[CH2:3]4)=[CH:23][CH:22]=3)[O:20][C:19]2=[N:21][C:50](=[O:49])[CH:51]=1

Participants

6

Reactant 4

HCID 2734062(-)-EpichlorohydrinHCID 23234139Ethyl 4-fluorobut-2-ynoateHCID 685258634-(3,3,5,5-Tetramethyl-cyclohexyl)-phenolHCID 685292945-[4-(3,3,5,5-Tetramethyl-cyclohexyl)-phenoxymethyl]-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 59252541(S)-5-Fluoromethyl-2-[4-(3,3,5,5-tetramethyl-cyclohexyl)-phenoxymethyl]-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared from 5-[4-(3,3,5,5-tetramethyl-cyclohexyl)-phenoxymethyl]-4,5-dihydro-oxazol-2-ylamine (prepared from 4-(3,3,5,5-tetramethyl-cyclohexyl)-phenol and (R)-epichlorohydrin according to the procedures employed in Step 1 through 2 of Example 1) and 4-fluoro-but-2-ynoic acid ethyl ester (see Example 105) according to the procedures described in Example 95. [α]D25 −21.40 (c 0.5, CHCl3).

Sources & evidence

ORD record
ord-b21e3519c934478c82ae3fb9f3350913
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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