Triethylamine → HCID 58864454, compound

HRID 1177816Notes

Reaction equation

HRID 1177816 reaction equation
C[Si](I)(C)C.[CH3:6][O:7][C:8](=[O:33])[C@H:9]([NH:22]C(OCC1C=CC=CC=1)=O)[CH2:10][C:11]1[C:20]([Br:21])=[CH:19][C:14]2[NH:15][C:16](=[O:18])[O:17][C:13]=2[CH:12]=1.C(N(CC)CC)C>C(#N)C>[CH3:6][O:7][C:8](=[O:33])[C@H:9]([NH2:22])[CH2:10][C:11]1[C:20]([Br:21])=[CH:19][C:14]2[NH:15][C:16](=[O:18])[O:17][C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85247Trimethylsilyl iodideHCID 25136129HCID 25136129, compound

Product 1

HCID 58864454HCID 58864454, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyliodide (73 mL, 0.73 mmol) was added to a solution of azotropically dried (R)-2-benzyloxycarbonylamino-3-(5-bromo-2-oxo-2,3-dihydro-benzooxazol-6-yl)-propionic acid methyl ester (146 mg, 0.33 mmol) in acetonitrile (10 mL) at room temperature, and the resulting mixture was stirred at room temperature for 2 h. Triethylamine (0.12 mL) was added and the mixture was stirred at room temperature for 15 min. The solvents were removed in vacuo, and the residue was extracted with ethyl acetate. The combined organics were washed with sodium bicarbonate and brine, dried over sodium sulfate and filtered. Solvents were removed and the residue was used directly in the next step. Mass spec. 315.10 (MH)+.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 min
  2. customThe solvents were removed in vacuo
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe combined organics were washed with sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customSolvents were removed

Sources & evidence

ORD record
ord-9162b96a8ded4a7eae87080037f45f55
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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