Triethylamine → HCID 11797917, compound

HRID 1720859Notes

Reaction equation

HRID 1720859 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:22])[C@H:6]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[NH:7][C:8](=[O:13])[C:9]([NH2:12])([CH3:11])[CH3:10])[CH3:3].C(N(CC)CC)C.[C:30]([S:33][C@@H:34]([CH:38]([CH3:40])[CH3:39])[C:35](O)=[O:36])(=[O:32])[CH3:31].ON1C2N=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.O>[CH2:2]([O:4][C:5](=[O:22])[C@H:6]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)[NH:7][C:8](=[O:13])[C:9]([NH:12][C:35](=[O:36])[C@@H:34]([S:33][C:30](=[O:32])[CH3:31])[CH:38]([CH3:40])[CH3:39])([CH3:11])[CH3:10])[CH3:3]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 181649HOAtHCID 10654866(2S)-2-(acetylsulfanyl)-3-methylbutanoic acidHCID 70094289HCID 70094289, compound

Product 1

HCID 11797917HCID 11797917, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(2-amino-2-methyl-1-oxopropyl)-L-tyrosine ethyl ester monohydrochloride (1.33 g, 3.70 mmol) in dimethylformamide (50 mL) and triethylamine (0.52 mL, 3.70 mmol) is added (S)-2-acetylthio-3-methylbutanoic acid (0.65 g, 3.70 mmol). To this mixture is added 1-hydroxy-7-azabenzotriazole (0.55 g, 4.07 mmol) and 1,3-dicyclohexylcarbodiimide (0.84 g, 4.07 mmol). The mixture is stirred overnight and then water (50 mL) is added to the mixture. The solution is extracted with ethyl acetate (3×50 mL). The combined organic layers are washed with a saturated solution of sodium bicarbonate (20 mL), brine, dried over magnesium sulfate and the solvent is removed to give a yellow foam. The foam is purified by flash chromatography (SiO2 :hexane/ethyl acetate, 6:4) to give as a white solid N-[2-(2(S)-acetylthio-3-methyl-1-oxobutylamino)-2-methyl-1-oxopropyl]-L-tyrosine ethyl ester, m.p. 137°-138° C., the compound of formula II wherein R1 is 4-hydroxyphenyl, R2 is ethyl, R3 is acetyl, R4 is isopropyl, and R6 and R7 are methyl.

Workup

  1. extractionThe solution is extracted with ethyl acetate (3×50 mL)
  2. washThe combined organic layers are washed with a saturated solution of sodium bicarbonate (20 mL), brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent is removed
  5. customto give a yellow foam
  6. customThe foam is purified by flash chromatography (SiO2 :hexane/ethyl acetate, 6:4)

Sources & evidence

ORD record
ord-39eb7d58e8714d34978cb5eb7b891fac
Source dataset
uspto-grants-1996_04
Patent number
US05508266

Reaction notes

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