Ethyl 4-fluorobut-2-ynoate → (S)-5-Fluoromethyl-2-[4-(1,1,3,3-tetramethyl-butyl)-phenoxymethyl]-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237859Notes

Reaction equation

HRID 237859 reaction equation
[CH3:1][C:2]([C:9]1[CH:22]=[CH:21][C:12]([O:13][CH2:14][C@H:15]2[O:19][C:18]([NH2:20])=[N:17][CH2:16]2)=[CH:11][CH:10]=1)([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].C([O:25][C:26](=O)[C:27]#[C:28][CH2:29][F:30])C>C(Cl)(Cl)Cl>[F:30][CH2:29][C:28]1[N:17]2[CH2:16][C@@H:15]([CH2:14][O:13][C:12]3[CH:21]=[CH:22][C:9]([C:2]([CH3:1])([CH3:8])[CH2:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[CH:10][CH:11]=3)[O:19][C:18]2=[N:20][C:26](=[O:25])[CH:27]=1

Participants

4

Reactant 2

HCID 23234139Ethyl 4-fluorobut-2-ynoateHCID 68529278(S)-5-(4-(1,1,3,3-tetramethyl-butyl)-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 59252486(S)-5-Fluoromethyl-2-[4-(1,1,3,3-tetramethyl-butyl)-phenoxymethyl]-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-(1,1,3,3-tetramethyl-butyl) -phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (see Example 27) and 4-fluoro-but-2-ynoic acid ethyl ester (see Example 105) employing the procedure described in Example 95. [α]D25 −28.00 (c 0.5, CHCl3).

Sources & evidence

ORD record
ord-2f7da6e8114c4b02a70591e81e005715
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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