Triethylamine → HCID 15870014, compound

HRID 618780Notes

Reaction equation

HRID 618780 reaction equation
C1(CO[C:9]([N:11]2[CH2:20][CH2:19][N:18]3[CH:13]([CH2:14][O:15][C:16]4[CH:24]=[C:23]([N:25]5[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]5=[O:35])[CH:22]=[CH:21][C:17]=43)[CH2:12]2)=[O:10])C=CC=CC=1.C(N(CC)CC)C.[CH2:43]([O:50][CH2:51]C(Cl)=O)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CO.C(Cl)Cl.[Pd]>[C:44]1([CH2:43][O:50][CH2:51][C:9]([N:11]2[CH2:20][CH2:19][N:18]3[CH:13]([CH2:14][O:15][C:16]4[CH:24]=[C:23]([N:25]5[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]5=[O:35])[CH:22]=[CH:21][C:17]=43)[CH2:12]2)=[O:10])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 158700138-[5-(S)-[(Acetylamino)methyl]-2-oxo-3-oxazolidinyl]-1,2,4a,5-tetrahydropyrazino[2,1-c][1,4]benzoxazine-3(4H)-carboxylic acid phenylmethyl ester

Product 1

HCID 15870014HCID 15870014, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a flask containing 8-[5-(S)-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-1,2,4a, 5-tetrahydropyrazino[2,1-c][1,4]benzoxazine-3(4H)-carboxylic acid phenylmethyl ester (EXAMPLE 1, 150 mg, 0.31 mmol) in methanol (5 mL) and methylene chloride (5 mL) is introduced 10% palladium on carbon (70 mg). The mixture is placed under a hydrogen balloon for 17 hours, filtered through celite, and concentrated in vacuo. The residue is dissolved in methylene chloride (10 mL) and triethylamine (0.09 mL, 0.62 mmol) and benzyloxyacetyl chloride (0.06 mL, 0.40 mmol) are added at 0° C. under an inert atmosphere. The reaction is warmed to ambient temperature, stirred for 15 hours, washed with water (10 mL) and saline, concentrated in vacuo, and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (96/4). The appropriate fractions are combined (Rf= 0.46, TLC, chloroform/methanol, 90/10) and concentrated in vacuo to give the title compound, NMR (CDCl3) 7.36-7.29, 6.96-6.94, 6.85, 6.70, 4.69, 4.60, 4.50, 4.23-4.15, 3.97-3.91, 3.70-3.52, 3.27, 2.99, 2.82, 2.65, 2.44, 1.98.

Workup

  1. customfor 17 hours
  2. filtrationfiltered through celite
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in methylene chloride (10 mL)
  5. washwashed with water (10 mL) and saline
  6. concentrationconcentrated in vacuo
  7. customchromatographed on silica gel (230-400 mesh, 100 mL)
  8. washeluting with chloroform/methanol (96/4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc363bf8f2d649208645b91b12612b40
Source dataset
uspto-grants-1999_09
Patent number
US05955460

Reaction notes

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