(Diethylamino)sulfur trifluoride → HCID 67171070, compound

HRID 1918293Notes

Reaction equation

HRID 1918293 reaction equation
C[O:2][C:3]([C:5]1([NH:13][C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[CH:16]=2)[CH2:10][CH2:9][CH:8]([CH2:11]O)[CH2:7][CH2:6]1)=[O:4].C(N(S(F)(F)[F:40])CC)C>C(Cl)Cl>[F:40][CH2:11][CH:8]1[CH2:9][CH2:10][C:5]([NH:13][C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=3)[CH:16]=2)([C:3]([OH:2])=[O:4])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 70872163HCID 70872163, compound

Product 1

HCID 67171070HCID 67171070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of step 1 of example 58 (100 mg, 0.220 mmol) was dissolved in DCM (2 ml), diethylaminosulfur trifluoride (35 mg, 0.22 mmol) was added and the mixture was stirred at room temperature for 72 h. The mixture was partitioned between EA and aqueous sodium hydrogencarbonate solution. The aqueous phase was extracted with EA, the combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) and hydrolyzed in analogy to step 4 of example 1 to yield the title compound.

Workup

  1. customThe mixture was partitioned between EA and aqueous sodium hydrogencarbonate solution
  2. extractionThe aqueous phase was extracted with EA
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel chromatography (HEP/EA gradient) and hydrolyzed in analogy to step 4 of example 1

Sources & evidence

ORD record
ord-6caaa1171dab44c9a646fda0af529bbe
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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