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

HRID 1697426Notes

Reaction equation

HRID 1697426 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-e40fd17fbefe4aecabe9a4015f1651cf
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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