Formaldehyde → HCID 66865144, compound

HRID 1192906Notes

Reaction equation

HRID 1192906 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C:16]2([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:19][NH:18][CH2:17]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:27]=O>C(O)=O>[CH3:27][N:18]1[CH2:19][CH2:20][C:16]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])([NH:15][S:12]([C:9]2[CH:10]=[CH:11][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:7][CH:8]=2)(=[O:13])=[O:14])[CH2:17]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 66865394HCID 66865394, compound

Product 1

HCID 66865144HCID 66865144, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ethyl 2-(3-(4-pentylphenylsulfonamido)pyrrolidin-3-yl)acetate (55 mg, 0.14 mmol) in formic acid (2 mL) was added formalin (15 μL, 0.16 mL). The solution was heated to 110° C. for 2 h. The mixture was concentrated and dissolved into CH2Cl2 (25 mL) and washed with sat. bicarbonate (2×5 mL), H2O (5 mL), dried over MgSO4 and concentrated to dryness to give the title compound as a brown oil (40 mg, 71%). MS ESI 397.2 [M+H]+, calcd for [C20H32N2O4S+H]+ 397.21.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved into CH2Cl2 (25 mL)
  3. washwashed with sat. bicarbonate (2×5 mL), H2O (5 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-00325168ac6448239a996ba253154afa
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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