Formaldehyde → HCID 54704627, compound

HRID 2214646Notes

Reaction equation

HRID 2214646 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].[CH2:8]=O.[Cl:10][C:11]1[CH:12]=[C:13]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:14][N:15]([CH3:27])[C:16](=[O:26])[CH:17]=[C:18]1[C:22](=[O:23])OC(C)(C)[O:19]1>CO>[Cl:10][C:11]1[CH:12]=[C:13]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:14][N:15]([CH3:27])[C:16]([C:17]1[CH2:8][N:5]([CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])[C:22](=[O:23])[C:18]=1[OH:19])=[O:26]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 69655735N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide

Product 1

HCID 54704627HCID 54704627, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-aminoacetaldehyde dimethylacetal (0.526 g mL, 5.0 mmol) and paraformaldehyde 90.15 g, 5 mmol) in MeOH (10 mL) at 55° C. was added N-(3,4-dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide (1.715 g, 5.0 mmol). After 45 min, the reaction mixture was cooled and purified by preparative HPLC on a C18 reverse phase column using acetonitrile (40–50%)/water (0.1% TFA) as eluent. The fractions containing the desired product were combined, concentrated and lyophilized to yield the title compound as an amber oil (0.68 g, 34% yield). 1H NMR (300 MHz, CDCl3) δ: 10.81 (bs, 1H), 7.42 (d, 1H, J=8.1), 7.35 (d, 1H, J=1.8), 7.10 (dd, 1H, J=8.1, J=1.8), 4.59 (s, 2H), 4.47 (t, 1H, J=5.1), 4.27 (s, 2H), 3.59 (d, 2H, J=5.1), 3.38 (s, 6H), 3.02 (s, 3H). HRMS (M+Na) calcd for C17H20N2Cl2O5Na: 425.0647. found: 425.0647.

Workup

  1. temperaturethe reaction mixture was cooled
  2. custompurified by preparative HPLC on a C18 reverse phase column
  3. additionThe fractions containing the desired product
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ebf7de586d2745f59afd768089db16d1
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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