Benzyl Alcohol → N-tert-butoxycarbonylphenylalanine benzyl ester

HRID 1611674Notes

Reaction equation

HRID 1611674 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20](O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:20]([O:18][C:17](=[O:19])[C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 128332N-tert-butoxycarbonylphenylalanine benzyl esterYield 82.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-L-phenylalanine (30.0 g, 113 mmol) and benzyl alcohol (14.0 mL, 136 mmol) in methylene chloride (200 mL), were added successively 4-dimethylaminopyridine (1.38 g, 11.3 mmol) and WSCI.HCl (26.0 g, 136 mmol) under ice-cooling, and the mixture was stirred for 63 hr while gradually raising the temperature to room temperature. The solvent was distilled away from the reaction solution under reduced pressure, and water (200 mL) was added to the residue. The mixture was extracted with ethyl acetate (400 mL). The obtained extract solution was washed with 0.5N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution, water and saturated brine (each 200 mL), and dried (anhydrous magnesium sulfate) and concentrated under reduced pressure. The obtained residue was recrystallized from hexane to give the title compound (33.1 g, 82%) as white crystals.

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled away from the reaction solution under reduced pressure, and water (200 mL)
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with ethyl acetate (400 mL)
  5. extractionThe obtained extract solution
  6. washwas washed with 0.5N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution, water and saturated brine (each 200 mL), and
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was recrystallized from hexane

Sources & evidence

ORD record
ord-79b2b02f009c4eecb3a8c6e2007f1e7c
Source dataset
uspto-grants-2006_01
Patent number
US06989401B2

Reaction notes

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