Sulfuric acid magnesium salt (1:1) → HCID 18451932, compound

HRID 1271486Notes

Reaction equation

HRID 1271486 reaction equation
[NH2:1][CH2:2][CH:3]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S([O-])([O-])(=O)=O.[Mg+2].[CH:24]1([CH:27]=O)[CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C.C(O)(=O)C>[CH:24]1([CH2:27][NH:1][CH2:2][CH:3]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:26][CH2:25]1

Participants

8

Reactant 5

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 123114CyclopropanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 18451931Ethyl 3-[(2-amino-1-phenylethyl)amino]propanoate

Product 1

HCID 18451932HCID 18451932, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of ethyl 3-[(2-amino-1-phenylethyl)amino]propanoate (6.38 g, 27.0 mmol), magnesium sulfate (10 g, 83.1 mmol), and cyclopropanecarboxaldehyde (2.02 mL, 27.2 mmol) in dichloroethane (200 mL) was adjusted to pH 6 with acetic acid. After 1 h, sodium triacetoxyborohydride (5.72 g, 27.0 mmol) was added. After an additional 30 min, saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography [100% dichloromethane→95% dichloromethane/5% (10% ammonium hydroxide/methanol)] gave the title compound (3.14 g). MS 291 (M+1).

Workup

  1. waitAfter an additional 30 min
  2. extractionthe mixture was extracted with dichloromethane (3×)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography [100% dichloromethane→95% dichloromethane/5% (10% ammonium hydroxide/methanol)]

Sources & evidence

ORD record
ord-cbdcef14f2f240fabbfe897f7cc0b236
Source dataset
uspto-grants-2007_04
Patent number
US07205292B2

Reaction notes

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