Formaldehyde → HCID 66864958, compound

HRID 1192914Notes

Reaction equation

HRID 1192914 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][NH:18][CH2:17]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:26]=O>C(O)=O>[CH3:26][N:18]1[CH2:19][C:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])([NH:15][S:12]([C:9]2[CH:8]=[CH:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:11][CH:10]=2)(=[O:14])=[O:13])[CH2:17]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 66864756HCID 66864756, compound

Product 1

HCID 66864958HCID 66864958, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
110 °C

Procedure

Ethyl 2-(3-(4-pentylphenylsulfonamido)azetidin-3-yl)acetate (35 mg, 0.095 mmol) was dissolved into formic acid (2 mL). The solution was treated with formaldehyde (16 mg of 36% solution, 0.19 mmol). The mixture was stirred at 110° C. for 2 h. Solvent was removed under vacuum. The residue was added CH2Cl2(10 mL) and washed with saturated sodium bicarbonate (3×5 mL) and H2O (10 mL) dried over MgSO4 and concentrated. The residue was loaded onto a silica gel column and eluted with EtOAc/hexane (30% to 50%) to obtain the title compound as a white powder (20 mg, 55%). 1H NMR (400 MHz, CDCl3) δ 7.76 (d, 2H, J=7.6 Hz), 7.30 (d, 2H, J=7.6 Hz), 4.03 (q, 2H, J=7.2 Hz), 3.36 (d, 2H, J=7.2 Hz), 3.23 (d, 2H, J=7.2 Hz), 2.95 (s, 2H), 2.68 (t, 2H, J=7.6 Hz), 2.30 (s, 3H), 1.67-1.60 (m, 2H), 1.33 (br, 4H), 1.19 (t, 3H, J=7.2 Hz), 0.92 (m, 3H); MS ESI 383.2 [M+H]+, calcd for [C19H30N2O4S+H]+383.20.

Workup

  1. customSolvent was removed under vacuum
  2. additionThe residue was added CH2Cl2(10 mL)
  3. washwashed with saturated sodium bicarbonate (3×5 mL) and H2O (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. washeluted with EtOAc/hexane (30% to 50%)

Sources & evidence

ORD record
ord-18ebf8c1383f4621a07c0dd22080a3ab
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

Loading…