(Diethylamino)sulfur trifluoride → HCID 54398697, compound

HRID 1935630Notes

Reaction equation

HRID 1935630 reaction equation
O[CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:12]3[CH2:16][C@H:15]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:14][C:13]3=[O:22])[CH:9]=2)[N:4]1[CH:23]=[O:24].C(N(S(F)(F)[F:31])CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:31][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:12]3[CH2:16][C@H:15]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[O:14][C:13]3=[O:22])[CH:9]=2)[N:4]1[CH:23]=[O:24]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluoride2×HCID 516892Sodium BicarbonateHCID 86585983HCID 86585983, compound

Product 1

HCID 54398697HCID 54398697, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-70 °C

Procedure

A stirred mixture of the product from Step 11 (0.085 g, 0.255 mmol)) and CH2Cl2 (10 ml), under nitrogen is cooled to −70° C. and treated, dropwise stirring 2 min, with a solution of (diethylamino)sulfur trifluoride (0.07 ml, 0.53 mmol) in CH2Cl2 (1 ml). The mixture is allowed to warm to ambient temperature slowly during 3 h. Additional CH2Cl2 (10 ml) is added and the mixture is kept at ambient temperature for 20 h, cooled to −70° C. and treated with 0.07 ml of additional DAST. It is kept at −70° C. for 1 h and at ambient temperature for 4 h, mixed with ice cold, saturated NaHCO3 and extracted with EtOAc. The extracts are washed with water and brine, dried (MgSO4) and concentrated. Chromatography of the residue on silica gel with 3.5% MeOH—CH2Cl2 gave 0.036 g of the titled product: HRMS (FAB) calcd for C16H18FN3O4+H 336.1359, found 336.1351; 1H NMR [300 MHz, (CD3)2SO] δ1.81 (s, 3H), 2.85, 3.00 (m, m, 1H), 3.38 (m, 3H), 3.71 (m, 1H), 4.06 (m, 1H), 4.30-4.88 (m, 4H), 7.30 (m, 1H), 7.43, 7.87 (d, d, 1H), 7.50 (m, 1H), 8.23 (t, 1H), 8.45, 9.00 (s, s, 1H).

Workup

  1. additiontreated
  2. temperatureto warm to ambient temperature slowly during 3 h
  3. temperaturecooled to −70° C.
  4. waitIt is kept at −70° C. for 1 h and at ambient temperature for 4 h
  5. extractionextracted with EtOAc
  6. washThe extracts are washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-20f5b711b41d4de0bcb47b609153cbcc
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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