Triethylamine → HCID 86636116, compound

HRID 1401340Notes

Reaction equation

HRID 1401340 reaction equation
Cl[C:2]1[C:7]2[S:8][C:9]([C:11]3[N:16]=[C:15]([CH2:17][N:18]([CH2:26][CH2:27][O:28][CH3:29])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:14]=[CH:13][CH:12]=3)=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[N+:30]([C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([F:40])[CH:34]=1)([O-:32])=[O:31].CCN(CC)CC>C1(OC2C=CC=CC=2)C=CC=CC=1.C1COCC1.CCOC(C)=O>[F:40][C:35]1[CH:34]=[C:33]([N+:30]([O-:32])=[O:31])[CH:38]=[CH:37][C:36]=1[O:39][C:2]1[C:7]2[S:8][C:9]([C:11]3[N:16]=[C:15]([CH2:17][N:18]([CH2:26][CH2:27][O:28][CH3:29])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:14]=[CH:13][CH:12]=3)=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 98252-Fluoro-4-nitrophenolHCID 86636115HCID 86636115, compound

Product 1

HCID 86636116HCID 86636116, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 7583Diphenyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 57 (1.43 g, 3.3 mmol) and 2-fluoro-4-nitrophenol (3) (1.03 g, 6.61 mmol) in diphenyl ether (30 mL) were stirred overnight at 160° C. The reaction mixture was cooled down to room temperature, diluted with THF (30 mL), treated with Et3N (1.38 mL, 9.9 mmol) and Boc-anhydride (1.08 g, 4.95 mmol) and stirred at room temperature for 2 h. It was then diluted with EtOAc (100 mL) and washed with saturated NaHCO3 (100 mL). The organic phase was collected, dried over Na2SO4, filtered and concentrated. Obtained crude product was purified by flash chromatography (using the gradient 70-100% EtOAc in hexanes as an eluent), yielding 58 (850 mg, 47% yield). MS (m/z): 555.2 (M+1).

Workup

  1. washwashed with saturated NaHCO3 (100 mL)
  2. customThe organic phase was collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customObtained crude product
  7. customwas purified by flash chromatography (

Sources & evidence

ORD record
ord-4a8e307ac0de4493a6917cbcd0f1e9ba
Source dataset
uspto-grants-2014_12
Patent number
US08907091B2

Reaction notes

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