Triethylamine → HCID 86636116, compound

HRID 1475568Notes

Reaction equation

HRID 1475568 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[S:23][C:22]3[C:24](Cl)=[CH:25][CH:26]=[CH:27][C:21]=3[CH:20]=2)[N:14]=1)[CH2:8][CH2:9][O:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].[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>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[S:23][C:22]3[C:24]([O:39][C:36]4[CH:37]=[CH:38][C:33]([N+:30]([O-:32])=[O:31])=[CH:34][C:35]=4[F:40])=[CH:25][CH:26]=[CH:27][C:21]=3[CH:20]=2)[N:14]=1)[CH2:8][CH2:9][O:10][CH3:11])([CH3:4])([CH3:3])[CH3:2]

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-0158079f6c324ad2bb5ef5f06f666241
Source dataset
uspto-grants-2015_04
Patent number
US09018378B2

Reaction notes

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