Dimethyl Sulfoxide → HCID 58180954, compound

HRID 1772808Notes

Reaction equation

HRID 1772808 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][C@H:15]1[CH3:27].C(N(CC)CC)C>C(Cl)Cl>[CH3:27][C@H:15]1[N:14]([CH2:13][CH:12]=[O:11])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58180901HCID 58180901, compound

Product 1

HCID 58180954HCID 58180954, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Dimethyl sulfoxide (0.732 mL, 10.3 mmol) was added to a solution of oxalyl chloride (0.582 mL, 6.88 mmol) in DCM (13 mL) at −78° C. After stirring for 10 minutes, tert-butyl (3R)-4-(2-hydroxyethyl)-3-methylpiperazine-1-carboxylate (1.4 g, 5.7 mmol) in DCM (6.6 mL) was added over 15 minutes. The reaction was stirred at −78° C. for 1 hour, then triethylamine (3.99 mL, 28.6 mmol) was added. The reaction was stirred, with warming to room temperature, for 1 hour. The reaction mixture was diluted with DCM, washed twice with water and once with brine, dried over sodium sulfate and concentrated to afford product, used without further purification (1.20 g, 86%). 1H NMR (300 MHz, CDCl3): δ 9.72 (t, 1H), 3.90-3.65 (m, 2H), 3.43 (d, 1H), 3.15 (ddd, 1H), 3.04 (dd, 1H), 2.89-2.67 (m, 2H), 2.52-2.34 (m, 2H), 1.46 (s, 9H), 1.02 (d, 3H); LCMS (M+H2O+H)+: 261.2.

Workup

  1. stirringThe reaction was stirred at −78° C. for 1 hour
  2. stirringThe reaction was stirred
  3. washwashed twice with water and once with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford product
  7. customused without further purification (1.20 g, 86%)

Sources & evidence

ORD record
ord-81ef580d9e8b46c8942c82af39a0c9fb
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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