Potassium Carbonate → HCID 54278276, compound

HRID 1358593Notes

Reaction equation

HRID 1358593 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C([O-])([O-])=O.[K+].[K+].[CH:28]1([CH2:34]Br)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:34][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 7019130Boc-Tyr-OMe

Product 1

HCID 54278276HCID 54278276, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of N-(tert-butoxycarbonyl)-L-tyrosine methyl ester (356 mg), K2CO3 (830 mg), n-Bu4NI (89 mg) in DMF (5 ml) was added cyclohexylmethyl bromide (202 μl) and the mixture was stirred for 1 day at room temperature. After addition of brine (40 ml), the resulting mixture was extracted with AcOEt. The extract was dried over Na2SO4 and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluent; 9:1, Hexane/AcOEt→1:1, Hexane/AcOEt) to give N-(tert-butoxycarbonyl)-O-cyclohexylmethyl-L-tyrosine methyl ester (470 mg). The obtained compound (347 mg) was dissolved in 3N HCl/AcOEt (5 ml) and the mixture was stirred overnight. The solvent and excess HCl was removed in vacuo to give O-(Cyclohexylmethyl)-L-tyrosine methyl ester, hydrochloride salt.

Workup

  1. extractionthe resulting mixture was extracted with AcOEt
  2. dry with materialThe extract was dried over Na2SO4
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by column chromatography on silica gel (eluent; 9:1, Hexane/AcOEt→1:1, Hexane/AcOEt)

Sources & evidence

ORD record
ord-822d0a44d2ca413cb3dd2c75d92a621e
Source dataset
uspto-grants-2003_07
Patent number
US06596752B1

Reaction notes

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