tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate → tert-Butyl (5S)-5-(2-tert-butoxy-2-oxoethyl)-3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

HRID 1486853Notes

Reaction equation

HRID 1486853 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CCCCCC.C(O)C>[C:1]([O:5][C:6](=[O:27])[CH2:7][C@@:8]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[CH2:9]1)([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 118292884tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

Product 1

HCID 131736824tert-Butyl (5S)-5-(2-tert-butoxy-2-oxoethyl)-3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylateYield 49.1%

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

A racemate of tert-butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(3-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (49.5 g) was fractionated by HPLC (column: CHIRALPAK AD (trade name), 50 mm ID×500 mm L, mobile phase: hexane/ethanol=850/150) to obtain the title compound (24.3 g) eluted at a larger retention time.

Sources & evidence

ORD record
ord-5a313b8ec8314a28875db4b5f7f7d973
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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