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

HRID 237860Notes

Reaction equation

HRID 237860 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].[CH2:23]([O:25][C:26](=O)[C:27]#[C:28][CH2:29][O:30]C)C>C(Cl)(Cl)Cl>[CH3:23][O:25][CH2:26][C:27]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:29](=[O:30])[CH:28]=1

Participants

4

Reactant 2

HCID 23249615Ethyl 4-methoxybut-2-ynoateHCID 68529278(S)-5-(4-(1,1,3,3-tetramethyl-butyl)-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 25070148(S)-5-Methoxymethyl-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-methoxy-but-2-ynoic acid ethyl ester (see Example 106) employing the procedure described in Example 95. [α]D25 −14.80 (c 0.5, CHCl3).

Sources & evidence

ORD record
ord-602fc5eb2b524c02b29fd90991a8c96f
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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