Methanesulfonyl chloride → HCID 58243380, compound

HRID 2361661Notes

Reaction equation

HRID 2361661 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:17][CH:16]([OH:18])[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:18][CH:16]1[CH2:15][N:14]([C:12]([N:8]2[CH2:9][CH2:10][CH2:11][N:5]([CH:1]3[CH2:4][CH2:3][CH2:2]3)[CH2:6][CH2:7]2)=[O:13])[CH2:17]1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 44462713HCID 44462713, compound

Product 1

HCID 58243380HCID 58243380, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-ol (100 mg, 0.395 mmol) in DCM (5 ml) at 0° C. was added TEA (120 mg, 1.2 mmol) and methansulphonyl chloride (110 mg, 0.94 mmol). The mixture was stirred for 2 h at RT, then diluted with DCM (15 ml) and washed with saturated NaHCO3 (10 ml). The organic layer was separated, dried (Na2SO4), filtered and concentrated providing the title compound as pale yellow solid (130 mg, 92%).

Workup

  1. washwashed with saturated NaHCO3 (10 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81b4ea67fd104248a5579d1d2c998862
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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