Ethanol → HCID 69834629, compound

HRID 849851Notes

Reaction equation

HRID 849851 reaction equation
[C:1]([O:5][C:6]([CH2:8][NH:9][C@H:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21](O)[CH3:22].Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[CH2:21]([O:12][C:11](=[O:13])[C@H:10]([NH:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:22]

Participants

6

Reactant 3

HCID 702EthanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53819702HCID 53819702, compound

Product 1

HCID 69834629HCID 69834629, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2R)-2-((tert-Butoxycarbonyl)methylamino)-3-phenylpropionic acid (4.0 g, 14.27 mmol) was dissolved in dichloromethane (5 ml) and ethanol (0.95 ml, 16.27 mmol). 4-Dimethylaminopyridine (0.19 g, 1.57 mmol) was added. The solution was cooled to 0° C. and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (2.98 g, 15.55 mmol) was added. The reaction mixture was stirred for 2 h at 0° C. for 16 h at room temp. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate/water (30 ml/30 ml). The phases were separated. The organic phase was washed with a saturated solution of sodium hydrogencarbonate and water and dried over magnesium sulfate. The crude product was purified by flash chromatography on silica (180 g) with ethyl acetate/heptane 1:2 to give 1.95 g of (2R)-2-((tert-butoxycarbonyl)methylamino)-3-phenylpropionic acid ethylester.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate/water (30 ml/30 ml)
  3. customThe phases were separated
  4. washThe organic phase was washed with a saturated solution of sodium hydrogencarbonate and water
  5. dry with materialdried over magnesium sulfate
  6. customThe crude product was purified by flash chromatography on silica (180 g) with ethyl acetate/heptane 1:2

Sources & evidence

ORD record
ord-d1fa0c0b87114f259618e694cd202e28
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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