Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl- → HCID 57558114, compound

HRID 1162938Notes

Reaction equation

HRID 1162938 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.[CH3:30][C:31]([O:34][C:35]([N:37]([CH2:39][C:40](O)=[O:41])[CH3:38])=[O:36])([CH3:33])[CH3:32]>C(Cl)Cl>[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][C:40](=[O:41])[CH2:39][N:37]([C:35]([O:34][C:31]([CH3:32])([CH3:30])[CH3:33])=[O:36])[CH3:38])[O:7]1

Participants

4

Reactant 2

HCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 11668552HCID 11668552, compound

Product 1

HCID 57558114HCID 57558114, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 7-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (800 mg, 1.98 mmol) obtained in step B of Example 1-14 was dissolved in methylene chloride (10 ml). Thereafter, Boc-sar-OH (449 mg, 2.37 mmol), N,N-dimethylaminopyridine (73 mg, 0.59 mmol), and WSCI (493 mg, 2.57 mmol) were added at 0° C. to the solution. The obtained mixture was stirred at a room temperature for 15 hours. Thereafter, the reaction mixture was concentrated under reduced pressure, and the obtained residue was then purified by silica gel chromatography (methylene chloride:methanol=20:1), so as to obtain N-tert-butoxycarbonyl-N-methylaminoacetic acid (R)-2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl ester (1.14 g, 100%) in the form of a colorless foaming substance.

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was then purified by silica gel chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-b173b7ae48474ae689ca8eecffb93e72
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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