(Diethylamino)sulfur trifluoride → HCID 57955523, compound

HRID 1880924Notes

Reaction equation

HRID 1880924 reaction equation
[CH2:1]([N:8]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:9][C:10](O)([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(S(F)(F)[F:30])CC>ClCCl>[CH2:1]([N:8]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:9][C:10]([F:30])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 57955558Ethyl 3-(benzyl(cyclohexyl)amino)-2-hydroxy-2-methylpropanoate

Product 1

HCID 57955523HCID 57955523, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To ethyl 3-(benzyl(cyclohexyl)amino)-2-hydroxy-2-methylpropanoate (7 g, 21.9 mmol) in 50 ml of dichlormethane at −78° C., was added DAST (4.3 ml, 32.8 mmol) dropwise. The reaction mixture was gradually warmed up to room temperature and stirred for 2 h. It was then diluted to dichloromethane, washed by NaHCO3, brine and water. Organic extract dried and concentrated to a residue, which was purified on silica gel column chromatographically (Hex/EtOAc=40:1 to 20:1) to give 6.8 g product (97%) as light yellow liquid. [M+H] calc'd for C19H28FNO2, 322; found 322.

Workup

  1. washwashed by NaHCO3, brine and water
  2. extractionOrganic extract
  3. customdried
  4. concentrationconcentrated to a residue, which
  5. customwas purified on silica gel column chromatographically (Hex/EtOAc=40:1 to 20:1)

Sources & evidence

ORD record
ord-5443da2579d7442fbe52beac92d51449
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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