Triethylamine → HCID 54319343, compound

HRID 2288767Notes

Reaction equation

HRID 2288767 reaction equation
[C@@H:1]12[CH2:8][N:7]([C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]4=[O:25])=[CH:11][C:10]=3[F:26])[CH2:6][C@@H:5]1[CH2:4][NH:3][CH2:2]2.C(N(CC)CC)C.[CH2:34]([O:41][CH2:42][C:43](Cl)=[O:44])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[F:26][C:10]1[CH:11]=[C:12]([N:15]2[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]2=[O:25])[CH:13]=[CH:14][C:9]=1[N:7]1[CH2:8][C@@H:1]2[C@@H:5]([CH2:4][N:3]([C:43](=[O:44])[CH2:42][O:41][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:2]2)[CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 54547617HCID 54547617, compound

Product 1

HCID 54319343HCID 54319343, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(S)-N-[[3-[4-[cis-3-(Carbobenzyloxy)-3,7-ciazabicyclo[3.3.0]octan-7-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (150 mg, 0.30 mmol), methylene chloride (5 mL), and methanol (10 mL) are combined with 10% palladium on carbon (30 mg) and placed under a hydrogen atmosphere (balloon) for 15 hours. The reaction is filtered through celite and concentrated in vacuo to give crude (S)-N-[[3-[4-[cis-3,7-diazabicyclo[3.3.0]octan-7-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide. The crude amine is taken up in methylene chloride (15 mL), cooled to 0° C., and triethylamine (0.09 mL, 0.67 mmol) and benzyloxyacetyl chloride (0.06 mL, 0.40 mmol) are added. The reaction is warmed to ambient temperature, stirred 15 hours, and diluted with methylene chloride (100 mL). The organic phase is washed with water (2×50 mL) and saline (150 mL), dried over sodium sulfate, concentrated in vacuo, and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (95/5). The appropriate fractions are combined (Rf =0.41, TLC, chloroform/methanol, 90/10) and concentrated in vacuo to give the title compound, mp 138-140° C.

Workup

  1. temperatureThe reaction is warmed to ambient temperature
  2. washThe organic phase is washed with water (2×50 mL) and saline (150 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customchromatographed on silica gel (230-400 mesh, 100 mL)
  6. washeluting with chloroform/methanol (95/5)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd36e1cc98ca4ab89c04ea8cb4176772
Source dataset
uspto-grants-2000_07
Patent number
US06090820

Reaction notes

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