Water → HCID 59000769, compound

HRID 1594021Notes

Reaction equation

HRID 1594021 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([O:16][C:17]([C:19]1[C:20]([C:43](=O)[NH2:44])=[C:21]([CH2:40][CH2:41][CH3:42])[N:22]2[C:27]=1[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:25][C:24]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[N:23]2)=[O:18])[CH3:15].CCN(CC)CC.O>C1COCC1>[CH2:14]([O:16][C:17]([C:19]1[C:20]([C:43]#[N:44])=[C:21]([CH2:40][CH2:41][CH3:42])[N:22]2[C:27]=1[C:26]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[CH:25][C:24]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[N:23]2)=[O:18])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 59000792HCID 59000792, compound

Product 1

HCID 59000769HCID 59000769, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetic anhydride (36 μL, 0.252 mmol) was added dropwise via syringe to a solution of 61 (100 mg, 0.229 mmol) and NEt3 (70 μL, 0.504 mmol) in THF (10 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 48 h. Water was added, the layers were separated, and the aqueous layer was extracted with EtOAc. The organic layers were pooled, washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to provide a yellow oil. Purification by flash chromatography (silica gel, 20% EtOAc/hexane) provided the title compound. 1H NMR (DMSO-d6) δ 0.74 (t, J=7.2 Hz, 3H), 0.94 (t, J=7.4 Hz, 3H), 1.78 (m, 2H), 3.03 (t, J=7.3 Hz, 2H), 3.59 (m, 6H), 3.75 (m, 4H), 7.02 (s, 1H), 7.48 (m, 5H). Mass Spectrum (ESI+) m/e=419.1 (M+H).

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a yellow oil
  8. customPurification by flash chromatography (silica gel, 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-d1d096eea2bf48e786a256d968623a0f
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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