Dimethyl Sulfoxide → HCID 58056620, compound

HRID 1260496Notes

Reaction equation

HRID 1260496 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([N:21]1[CH2:42][CH2:41][C:24]2([C:28](=[O:29])[N:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)[CH:23]([OH:43])[CH2:22]1)(=[O:20])=[O:19].C(N(CC)CC)C>C(Cl)Cl>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([N:21]1[CH2:42][CH2:41][C:24]2([C:28](=[O:29])[N:27]([C:30]3[CH:31]=[CH:32][C:33]([O:36][C:37]([F:39])([F:40])[F:38])=[CH:34][CH:35]=3)[CH2:26][CH2:25]2)[C:23](=[O:43])[CH2:22]1)(=[O:19])=[O:20]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 56602660HCID 56602660, compound

Product 1

HCID 58056620HCID 58056620, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In a 10 mL round-bottomed flask, oxalyl chloride (46.1 mg, 31.8 μl, 356 μmol) was combined with DCM (5 mL) to give a colorless solution. DMSO (27.8 mg, 25.3 μl, 356 μmol) was added drop wise at −78° C. The reaction was stirred for 15 min. A solution of 8-(2-chlorophenylsulfonyl)-6-hydroxy-2-(4-(trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one (124 mg, 246 μmol) in DCM (1 mL) was added. The reaction mixture was stirred for 30 min at −40° C. Triethylamine (74.6 mg, 103 μl, 737 μmol) was added drop wise and the reaction mixture was heated to r.t. and stirred for 3 h. The reaction mixture was poured into 15 mL DCM and washed with H2O (2×10 mL).The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by flash chromatography (0 to 100% AcOEt in heptane) to afford the title compound as an off-white solid (73 mg, 59%). MS (ESI): 503.1 (MH+).

Workup

  1. customto give a colorless solution
  2. stirringThe reaction mixture was stirred for 30 min at −40° C
  3. stirringstirred for 3 h
  4. washwashed with H2O (2×10 mL).The organic layers
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography (0 to 100% AcOEt in heptane)

Sources & evidence

ORD record
ord-db2666060ac7480a9f5527764a3d8c77
Source dataset
uspto-grants-2013_06
Patent number
US08470843B2

Reaction notes

Loading…