Carbon Tetrachloride → HCID 59520039, compound

HRID 1162941Notes

Reaction equation

HRID 1162941 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])[NH:15][C:16]3=[O:19])=[CH:11][CH:10]=2)[CH2:4]1.C(N(CC)C(C)C)(C)C.C(Cl)(Cl)(Cl)Cl.[P:44]([O-:61])([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C(#N)C>[O:8]=[C:6]1[N:5]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:28])([F:27])[F:29])[NH:15][C:16]3=[O:19])=[CH:11][CH:10]=2)[CH2:4][C@H:3]([CH2:2][O:1][P:44]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:61])[O:7]1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 81531DiisopropylethylamineHCID 11668552HCID 11668552, compoundHCID 21904359Dibenzylphosphite

Product 1

HCID 59520039HCID 59520039, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

The 7-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (150 mg, 0.37 mmol) obtained in step B of Example 1-14 was dissolved in acetonitrile (5 ml). Thereafter, N,N-diisopropylethylamine ml, 2.96 mmol), carbon tetrachloride (0.706 ml, 7.4 mmol), N,N-dimethylaminopyridine (14 mg, 0.22 mmol), and dibenzyl phosphite (0.410 ml, 1.86 mmol) were added to the solution. The obtained mixture was stirred at 50° C. for 15 hours. Thereafter, the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=1:5), so as to obtain phosphate dibenzyl ester (R)-2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]-oxazolidin-5-ylmethyl ester (85 mg, 34%) in the form of a colorless foaming substance.

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  2. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=1:5)

Sources & evidence

ORD record
ord-becf40ebc43c421aa6eddd5d210e472b
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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