Ethyl 4-methoxybut-2-ynoate → (S)-2-(4-tert-Butyl-phenoxymethyl)-5-methoxymethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237831Notes

Reaction equation

HRID 237831 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][C:8]([O:9][CH2:10][C@H:11]2[O:15][C:14]([NH2:16])=[N:13][CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([O:21][C:22](=O)[C:23]#[C:24][CH2:25][O:26]C)C>C(O)C>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([O:9][CH2:10][C@H:11]2[O:15][C:14]3=[N:16][C:25](=[O:26])[CH:24]=[C:23]([CH2:22][O:21][CH3:19])[N:13]3[CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 23249615Ethyl 4-methoxybut-2-ynoateHCID 67060987(S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 59252522(S)-2-(4-tert-Butyl-phenoxymethyl)-5-methoxymethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-oneYield 69.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-yl-amine (2.3 g, 9.26 mmol) (prepared according to the procedures employed in Step 1 through 2 of Example 1) in ethanol (35 mL) was added 1.7 g (12.04 mmol) of 4-methoxy-but-2-ynoic acid ethyl ester (prepared in accordance with the procedures as described in Larock, J Org Chem 2002, 67, 9318). This mixture was stirred at reflux for 6 hours and cooled. The reaction mixture was concentrated and loaded onto a silica gel column. Chromatography with 1-10% EtOH/CH2Cl2 provided 2.22 g of the title compound. [α]D25 −18.00 (c 0.5, CHCl3)

Workup

  1. customprepared in accordance with the procedures
  2. temperatureat reflux for 6 hours
  3. temperaturecooled
  4. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-5bf9747ee10a45a8a9281768bf60f468
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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