(Diethylamino)sulfur trifluoride → HCID 54250429, compound

HRID 1492115Notes

Reaction equation

HRID 1492115 reaction equation
C(N(S(F)(F)[F:7])CC)C.O[CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][C:17]([C:23]1([C:33]([OH:35])=[O:34])[CH2:28][NH:27][CH2:26][CH2:25][N:24]1[C:29]([CH3:32])([CH3:31])[CH3:30])=[N:18]2.C([O-])(O)=O.[Na+]>>[F:7][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][C:17]([C:23]1([C:33]([OH:35])=[O:34])[CH2:28][NH:27][CH2:26][CH2:25][N:24]1[C:29]([CH3:32])([CH3:31])[CH3:30])=[N:18]2

Participants

4

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 54248450HCID 54248450, compound

Product 1

HCID 54250429HCID 54250429, compoundYield 66%

Procedure

To a -78° C. solution of Diethylaminosulfur trifluoride (DAST) (0.06 ml, 0.42 mmol) in dry CH2C2 was slowly added a solution of 13 (50 mg, 0.14 mmol) in dry CH2C2 (3 ml). The solution was allowed to warm to room temperature and stirred for 1 h. Saturated aqueous NaHCO3 was added and the mixture was extracted with CH2Cl2. The organic phase was dried (MgSO4) and concentrated. The residue was purified by HPLC (Whatman Partisil M9 column, 90:10 CH2Cl2 :EtOAc) to afford the fluoroethyl derivative 14 (33 mg, 66%). 1H NMR d (ppm): 1.48 s (3 CH3), 3.36 dt (CH2), 3.56 dd (NCH2), 3.71 dd (NCH2), 4.69 dt (CH2), 6.99 d (CH arom), 7.11 d (CH arom), 7.46 dd (CH arom), 7.61 d (CH arom), 8.10 d (CH arom).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by HPLC (Whatman Partisil M9 column, 90:10 CH2Cl2 :EtOAc)

Sources & evidence

ORD record
ord-b0a02957ae024bafb1df213b01c5f87c
Source dataset
uspto-grants-1994_12
Patent number
US05372813

Reaction notes

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