Acetoxyacetic acid → (S)-2-Oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl acetoxyacetate

HRID 1162948Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].O[CH2:10][C@H:11]1[O:15][C:14](=[O:16])[N:13]([C:17]2[CH:26]=[C:25]3[C:20]([CH:21]=[C:22]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:37])([F:36])[F:35])[NH:23][C:24]3=[O:27])=[CH:19][CH:18]=2)[CH2:12]1>>[C:1]([O:4][CH2:5][C:6]([O:8][CH2:10][C@H:11]1[O:15][C:14](=[O:16])[N:13]([C:17]2[CH:26]=[C:25]3[C:20]([CH:21]=[C:22]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:36])([F:35])[F:37])[NH:23][C:24]3=[O:27])=[CH:19][CH:18]=2)[CH2:12]1)=[O:7])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 83766Acetoxyacetic acid

HCID 118536727-((S)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Product 1

HCID 57557960(S)-2-Oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl acetoxyacetate

Procedure

The title compound was synthesized by a condensation method similar to that of Step A of Example 3-1 using acetoxyacetic acid instead of Boc-Sar-OH and 7-((S)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Step B of Example 1-13 instead of 7-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Step B of Example 1-14.

Sources & evidence

ORD record: ord-5cc0737912e04e1683bbd1fd314fe9a9
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820693B2

Reaction notes

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