Methanesulfonyl chloride → HCID 86651906, compound

HRID 1772778Notes

Reaction equation

HRID 1772778 reaction equation
[OH:1][CH:2]([CH3:20])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1.CCN(C(C)C)C(C)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH3:30][S:31]([O:1][CH:2]([CH3:20])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67054912HCID 67054912, compound

Product 1

HCID 86651906HCID 86651906, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of benzyl 4-(2-hydroxypropyl)piperazine-1-carboxylate (from step 1, 1.7 g, 6.1 mmol) in DCM (20 mL) was added DIPEA (2.1 mL, 12 mmol) followed by methanesulfonyl chloride (0.70 mL, 9.0 mmol) at 0° C. The reaction was stirred at 0° C. for 2 h. The reaction was quenched with saturated NaHCO3 solution and extracted with DCM. The combined organic layers were washed with brine, dried over MgSO4 and concentrated to provide crude product (2.22 g) which was used in next step without further purification. LCMS calculated for C16H25N2O5S(M+H)+: m/z=357.1; Found: 357.3.

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution
  2. extractionextracted with DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ae22d9873b964d94b8a1f980554dabc4
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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