D-Tartaric acid → tert-butyl 4-((1R)-1-aminopropyl)-2-nitrobenzoate D-tartarate

HRID 554825Notes

Reaction equation

HRID 554825 reaction equation
[NH2:1][CH:2]([C:5]1[CH:17]=[CH:16][C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:7]([N+:18]([O-:20])=[O:19])[CH:6]=1)[CH2:3][CH3:4].[C:21]([OH:30])(=[O:29])[C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23]>CO>[C:21]([OH:30])(=[O:29])[C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23].[NH2:1][C@@H:2]([C:5]1[CH:17]=[CH:16][C:8]([C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])=[C:7]([N+:18]([O-:20])=[O:19])[CH:6]=1)[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 439655D-Tartaric acidHCID 67461906Tert-butyl 4-(1-aminopropyl)-2-nitrobenzoate

Product 1

HCID 86634888tert-butyl 4-((1R)-1-aminopropyl)-2-nitrobenzoate D-tartarateYield 65.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-(1-aminopropyl)-2-nitrobenzoate (5.6 g) in 98% hydrous methanol (112 ml), D-tartaric acid (1.8 g) was added at room temperature, and the mixture was stirred at 60° C. for 1 hour and further stirred at room temperature for 5 hours. The precipitated crystals were collected by filtration and dried to obtain the title compound (3.4 g) as a colorless crystal. A small amount of obtained crystal salt was conveted to corresponding free form, and optical purity of obtained dree form was determined by high performance liquid chromatography (HPLC), whereupon it was found to be 62.2% ee. The obtained crystals (3.4 g, 62.2% ee) were suspended in 80% hydrous methanol (68 ml), and the resulting suspension was stirred under heating and refluxed for 1 hour, then further stirred at room temperature for 5 hours. The precipitated crystals were collected by filtration and dried to obtain the title compound (2.7 g, 94.4% ee) as a colorless crystal. To improve the optical purity, the obtained crystals (2.7 g, 94.4%ee) were suspended in 80% hydrous methanol (54 ml), and the resulting suspension was stirred under heating and refluxed for 1 hour, then further stirred at room temperature for 5 hours. The precipitated crystals were collected by filtration and dried to obtain the title compound (2.5 g, 99.1% ee) as a colorless crystal.

Workup

  1. stirringfurther stirred at room temperature for 5 hours
  2. filtrationThe precipitated crystals were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-4e9039fd5d2748ea9741dce53603a009
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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