Aminoacetaldehyde dimethyl acetal → Methyl 4-chloro-3-{[[(2,2-dimethoxyethyl)amino](oxo)acetyl]amino}benzoate

HRID 337168Notes

Reaction equation

HRID 337168 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][C:13](=[O:19])[C:14]([O:16]CC)=O.[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23][NH2:24]>C(OCC)(=O)C.C(OCC)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][C:13](=[O:19])[C:14]([NH:24][CH2:23][CH:22]([O:25][CH3:26])[O:21][CH3:20])=[O:16]

Participants

5

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 28710241Methyl 4-chloro-3-{[ethoxy(oxo)acetyl]amino}benzoate

Product 1

HCID 66688946Methyl 4-chloro-3-{[[(2,2-dimethoxyethyl)amino](oxo)acetyl]amino}benzoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of methyl 4-chloro-3-{[ethoxy(oxo)acetyl]amino}benzoate (Example 330b, 11.2 g) dissolved in ethyl acetate (80 mL) was treated with aminoacetaldehyde dimethyl acetal (5.08 mL) under nitrogen. The resulting mixture was stirred at 20° C. for 3 h. The reaction mixture was diluted with diethyl ether (100 mL) and stirred at room temperature overnight. The solid formed was filtered off and dried under vacuum to afford the subtitle compound (12.64 g).

Workup

  1. stirringstirred at room temperature overnight
  2. customThe solid formed
  3. filtrationwas filtered off
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f359a4f5e0ab43db8198d2f4afdb33eb
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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