Dimethylformamide → N-[2-(t-butoxycarbonylamino)-2-methyl-1-oxopropyl]-L-tyrosine ethyl ester

HRID 1720860Notes

Reaction equation

HRID 1720860 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[NH2:6])[CH3:2].[C:16]([O:20]N[C@](C)(C(O)=O)C=C=O)([CH3:19])([CH3:18])[CH3:17].C1(N=[C:37]=[N:38][CH:39]2[CH2:44]CCC[CH2:40]2)CCCCC1.[OH:45]N1C2C=CC=CC=2N=N1.CN(C)[CH:57]=[O:58]>O>[CH2:1]([O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[NH:6][C:57](=[O:58])[C:39]([NH:38][C:37]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:45])([CH3:40])[CH3:44])[CH3:2]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 70364L-Tyrosine ethyl esterHCID 757711-HydroxybenzotriazoleHCID 86749438N-t-butoxy-carbonyl-alpha-methylalanine

Product 1

HCID 10810636N-[2-(t-butoxycarbonylamino)-2-methyl-1-oxopropyl]-L-tyrosine ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of L-tyrosine ethyl ester (2.10 g, 10.0 mmol) and N-t-butoxy-carbonyl-α-methylalanine (2.03 g, 10.0 mmol) in dimethylformamide (40 mL) is added 1,3-dicyclohexylcarbodiimide (2.26 g, 11.0 mmol) and 1-hydroxybenzotriazole (1.48 g, 11.0 mmol). The mixture is stirred overnight and then water (50 mL) is added. The aqueous phase is extracted with ethyl acetate (3×75 mL). The combined organic phases are washed with a saturated solution of sodium bicarbonate (25 mL), brine, dried over magnesium sulfate and the solvent is removed to give a light yellow oil. The oil is purified by flash chromatography (SiO2 :hexane/ethyl acetate) to afford N-[2-(t-butoxy-carbonylamino)-2-methyl-1-oxopropyl]-L-tyrosine ethyl ester as a white solid.

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate (3×75 mL)
  2. washThe combined organic phases are washed with a saturated solution of sodium bicarbonate (25 mL), brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent is removed
  5. customto give a light yellow oil
  6. customThe oil is purified by flash chromatography (SiO2 :hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7e947ae8125741a6b438075f257b0abd
Source dataset
uspto-grants-1996_04
Patent number
US05508266

Reaction notes

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