Methanesulfonyl chloride → HCID 76788404, compound

HRID 1949656Notes

Reaction equation

HRID 1949656 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH:9]1[CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][S:37]([CH3:36])(=[O:39])=[O:38])[CH:9]1[CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67212811HCID 67212811, compound

Product 1

HCID 76788404HCID 76788404, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing 112 (1.68 g, 4.60 mmol) and DIPEA (0.71 g, 5.53 mmol) in DCM (20 mL) was cooled to 0° C. MsCl (0.52 g, 4.60 mmol) was added. After 1 h, the reaction mixture was diluted with EtOAc and washed successively with dilute aqueous HCl, brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (1:1 to 1:3 hexanes/EtOAc) to afford 2.6 g (quant.) of 113.

Workup

  1. washwashed successively with dilute aqueous HCl, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash silica gel chromatography (1:1 to 1:3 hexanes/EtOAc)

Sources & evidence

ORD record
ord-4c8a22bc533343cfb879d5561692d7e3
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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