Triethylamine → HCID 57558028, compound

HRID 1162946Notes

Reaction equation

HRID 1162946 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:2]=[O:3].C(N(CC)CC)C.[OH:17][CH2:18][C@@H:19]1[O:23][C:22](=[O:24])[N:21]([C:25]2[CH:34]=[C:33]3[C:28]([CH:29]=[C:30]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:42]([F:45])([F:44])[F:43])[NH:31][C:32]3=[O:35])=[CH:27][CH:26]=2)[CH2:20]1.[Cl-].[NH4+]>ClCCl>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][NH:1][C:2]([O:17][CH2:18][C@@H:19]1[O:23][C:22](=[O:24])[N:21]([C:25]2[CH:34]=[C:33]3[C:28]([CH:29]=[C:30]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:42]([F:43])([F:45])[F:44])[NH:31][C:32]3=[O:35])=[CH:27][CH:26]=2)[CH2:20]1)=[O:3])[CH3:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 76283Ethyl isocyanatoacetateHCID 11668552HCID 11668552, compound

Product 1

HCID 57558028HCID 57558028, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl isocyanatoacetate (6.6 μL, 0.059 mmol) and triethylamine (10.3 μL, 0.074 mmol) were added to a solution of 7-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Step B of Example 1-14 (20 mg, 0.050 mmol) in dichloromethane, and the mixture was stirred at room temperature for four hours. Aqueous saturated ammonium chloride was added to the mixture, followed by extraction with dichloromethane. The extract was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by aminosilica gel column chromatography (methylene chloride:methanol=50:1) to obtain 24 mg (92%) of ethyl{(R)-2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethoxycarbonylamino}acetate as a colorless oil.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by aminosilica gel column chromatography (methylene chloride:methanol=50:1)

Sources & evidence

ORD record
ord-1aee97fd4def4299a15530ba0a831f05
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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