2,6-Lutidine → HCID 131715955, compound

HRID 1904442Notes

Reaction equation

HRID 1904442 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[NH:5][C:6]([O:8]C(C)(C)C)=[O:7].N1C(C)=[CH:33][CH:32]=[CH:31][C:30]=1C.[Si:37](OS(C(F)(F)F)(=O)=O)(C(C)(C)C)([CH3:39])[CH3:38].[Cl-].[NH4+]>ClCCl>[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:19])[N:5]([C:6]([O:8][SiH:37]([CH3:39])[CH3:38])=[O:7])[CH2:30][CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 11132998Boc-L-Lys(Z)-OMe

Product 1

HCID 131715955HCID 131715955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (1.0 ml) of Nα-t-butoxycarbonyl-Nε-benzyloxycarbonyllysine methyl ester (191.0 mg, 0.48 mmol) were added 2.6-lutidine (113 μl, 0.97 mmol) and t-butyldimethylsilyltrifluoromethane sulfonate (167 μl, 0.73 mmol). The mixture was stirred for 15 minutes in an argon atmosphere at room temperature. After addition of a saturated aqueous solution of ammonium chloride, the reaction mixture was extracted with ether and the ether layer was dried over anhydrous magnesium sulfate and filtered. After removal of the solvent in vacuo, Nα-butyldimethylsilyloxycarbonyl-Nε-benzyloxycarbonyllysine methyl ester was obtained (238 mg; yield, 100%).

Workup

  1. extractionthe reaction mixture was extracted with ether
  2. dry with materialthe ether layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customAfter removal of the solvent in vacuo

Sources & evidence

ORD record
ord-2cfa7d1b4fbc457dbe6bcb4b0fd3c358
Source dataset
uspto-grants-1989_06
Patent number
US04837349

Reaction notes

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