Methyl iodide → HCID 66864972, compound

HRID 1192915Notes

Reaction equation

HRID 1192915 reaction equation
[CH3:1][N:2]1[CH2:5][C:4]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])([NH:6][S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:3]1.[CH3:27][I:28]>C(Cl)Cl>[I-:28].[CH2:25]([O:24][C:22](=[O:23])[CH2:21][C:4]1([NH:6][S:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:14][CH:15]=2)(=[O:9])=[O:8])[CH2:5][N+:2]([CH3:27])([CH3:1])[CH2:3]1)[CH3:26]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 66864958HCID 66864958, compound

Product 1

HCID 66864972HCID 66864972, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-(1-methyl-3-(4-pentylphenylsulfonamido)azetidin-3-yl)acetate (10 mg, 0.026 mmol) was dissolved into CH2Cl2 (2 mL). The solution was treated with methyl iodide (37 mg, 0.26 mmol). The mixture was stirred at room temperature overnight. Solvent was removed under vacuum to obtain the title compound as a yellow solid (10 mg, 77%) which was used in the next step without purification. 1H NMR (400 MHz, CDCl3) δ 7.83 (d, 2H, J=8 Hz), 7.33 (d, 2H, J=8 Hz), 5.04 (m, 4H), 3.90 (q, 2H, J=7.2 Hz), 3.64 (s, 3H), 3.58 (m, 3H), 3.14 (s, 2H), 2.66 (t, 2H, J=8 Hz), 1.65-1.58 (m, 2H), 1.32 (br, 4H), 1.10 (t, 3H, J=7.2 Hz), 0.89 (m, 3H); MS ESI 397.2 [M]+, calcd for [C20H33N2O4S]+ 397.22.

Workup

  1. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-a3a73e912449499495a5a7a2c69414d3
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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