7-((S)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one → (S)-2-Oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl 3-hydroxy-2,2-bishydroxymethylpropionate

HRID 1162945Notes

Reaction equation

HRID 1162945 reaction equation
C([O:8][CH2:9][C:10]([CH2:23][O:24]CC1C=CC=CC=1)([CH2:14][O:15]CC1C=CC=CC=1)[C:11](O)=[O:12])C1C=CC=CC=1.[OH:32][CH2:33][C@H:34]1[O:38][C:37](=[O:39])[N:36]([C:40]2[CH:49]=[C:48]3[C:43]([CH:44]=[C:45]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=4[C:57]([F:60])([F:59])[F:58])[NH:46][C:47]3=[O:50])=[CH:42][CH:41]=2)[CH2:35]1.[H][H]>[Pd]>[OH:12][CH2:11][C:10]([CH2:23][OH:24])([CH2:14][OH:15])[C:9]([O:32][CH2:33][C@H:34]1[O:38][C:37](=[O:39])[N:36]([C:40]2[CH:49]=[C:48]3[C:43]([CH:44]=[C:45]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=4[C:57]([F:59])([F:58])[F:60])[NH:46][C:47]3=[O:50])=[CH:42][CH:41]=2)[CH2:35]1)=[O:8]

Participants

5

Reactant 3

HCID 118536727-((S)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneHCID 575579373-Benzyloxy-2,2-bis(benzyloxymethyl)propionic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 57557884(S)-2-Oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl 3-hydroxy-2,2-bishydroxymethylpropionate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Condensation was carried out by a method similar to that of Example 3-1 using 3-benzyloxy-2,2-bis(benzyloxymethyl)propionic acid obtained in Step B 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, and deprotection was carried out by a method similar to that of Example 1-36 using a 10% Pd—C catalyst in a hydrogen atmosphere to synthesize the title compound.

Workup

  1. customCondensation

Sources & evidence

ORD record
ord-d54666c7a719477380ffabff6b1493dc
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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