(Diethylamino)sulfur trifluoride → HCID 178480285, compound

HRID 717242Notes

Reaction equation

HRID 717242 reaction equation
[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)/[C:7](=[N:17]/[C:18](=[O:36])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=2[O:29][CH2:30][CH2:31][C:32](O)([CH3:34])[CH3:33])/[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:43])CC>C(Cl)Cl>[C:1]([C:5]1[N:9]([CH3:10])[N:8]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)/[C:7](=[N:17]/[C:18](=[O:36])[C:19]2[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][C:20]=2[O:29][CH2:30][CH2:31][C:32]([F:43])([CH3:33])[CH3:34])/[CH:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 178480287HCID 178480287, compound

Product 1

HCID 178480285HCID 178480285, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 43A (215 mg, 0.42 mmol) in CH2Cl2 (10 mL) was treated dropwise with DAST (66 μL, 0.504 mmol) at −78° C. The reaction mixture was allowed to warm up to room temperature for 4 hrs. The mixture was quenched with saturated NaHCO3 and extracted with EtOAc (2×). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 50% hexanes/EtOAc to 100% EtOAc to 9:1:0.1 EtOAc:MeOH:Et3N) to afford 48 mg (22%) of the title compound. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.45 (d, J=21.48 Hz, 6H) 1.50 (s, 9H) 1.82-1.99 (m, 3H) 2.19-2.37 (m, 3H) 3.67-3.83 (m, 2H) 4.14-4.23 (m, 1H) 4.24 (s, 3H) 4.48 (t, J=7.36 Hz, 2H) 4.80-4.97 (m, 1H) 5.48 (d, J=17.18 Hz, 1H) 6.97 (s, 1H) 7.13 (d, J=8.59 Hz, 1H) 7.74 (dd, J=7.98, 1.84 Hz, 1H) 8.08 (d, J=2.15 Hz, 1H); MS (DCI/NH3) m/z 514 (M+H)+.

Workup

  1. customThe mixture was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-84fc8f7df2ec4911a3e7ea18b108cad7
Source dataset
uspto-grants-2015_11
Patent number
US09193713B2

Reaction notes

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