(Diethylamino)sulfur trifluoride → HCID 131725257, compound

HRID 1611247Notes

Reaction equation

HRID 1611247 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C@@H:4](O)[CH:5]([C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[C:17]1[O:18][CH:19]=[CH:20][N:21]=1)=[O:11])[CH2:6][CH2:7][CH2:8][CH3:9].CCN(S(F)(F)[F:30])CC>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:23])[CH:4]([F:30])[CH:5]([C:10]([N:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[C:17]1[O:18][CH:19]=[CH:20][N:21]=1)=[O:11])[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 91157840HCID 91157840, compound

Product 1

HCID 131725257HCID 131725257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2(S)-hydroxy-3-(2(S)-oxazol-2-yl-pyrrolidin-1-carbonyl)-heptanoic acid methyl ester C-1 (5 mmol) in DCM (5 mL) is added DAST (15 mmol) at −20° C. The solution is stirred for 16 hours at rt. The reaction mixture is washed with aqueous NaHCO3 and brine, dried (Na2SO4) and concentrated then purified on silica gel (EtOAc/hexanes) to afford 2-(R/S)-fluoro-3-(2(S)-oxazol-2-yl-pyrrolidin-1-carbonyl)-heptanoic acid methyl ester C-2.

Workup

  1. washThe reaction mixture is washed with aqueous NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customthen purified on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-958e5b23ed2540f1978d2b2cfb0d722e
Source dataset
uspto-grants-2006_01
Patent number
US06987104B2

Reaction notes

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