Triethylamine → N-t-butyldimethylsilyloxycarbonylvaline methyl ester

HRID 1904449Notes

Reaction equation

HRID 1904449 reaction equation
C(N(CC)CC)C.[C:8]([SiH:12]([CH3:14])[CH3:13])([CH3:11])([CH3:10])[CH3:9].[CH3:15][O:16][C:17](=[O:29])[C@H:18]([CH:26]([CH3:28])[CH3:27])[NH:19][C:20]([O:22]CC=C)=[O:21].[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[CH3:15][O:16][C:17](=[O:29])[C@H:18]([CH:26]([CH3:27])[CH3:28])[NH:19][C:20]([O:22][Si:12]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:14])[CH3:13])=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 5072427tert-ButyldimethylsilaneHCID 11148605N-allyloxycarbonylvaline methyl ester

Product 1

HCID 13934325N-t-butyldimethylsilyloxycarbonylvaline methyl ester

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane solution (1.0 ml) of palladium (II) acetate (8.0 mg, 0.04 mmol) and triethylamine (15 μl, 0.11 mmol), t-butyldimethylsilane (179 μl, 1.1 mmol) was added and the mixture was stirred for 15 minutes at room temperature. To the resulting black suspension, a dichloromethane solution (1.0 ml) of N-allyloxycarbonylvaline methyl ester (154 mg, 0.72 mmol) was added and the mixture was stirred for an additional 15 hours. After a saturated aqueous solution of ammonium chloride was added to quench the reaction, extraction with ether was conducted and the ether layer was dried over anhydrous magnesium sulfate and filtered. By distilling off the solvent, N-t-butyldimethylsilyloxycarbonylvaline methyl ester was obtained in an amount of 207 mg (yield, 100%). The physical data for this compound were in agreement with those reported in Examples 4 and 9.

Workup

  1. stirringthe mixture was stirred for an additional 15 hours
  2. customto quench
  3. customthe reaction, extraction with ether
  4. dry with materialthe ether layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationBy distilling off the solvent

Sources & evidence

ORD record
ord-fe4e46c335624c189f7625a68b166344
Source dataset
uspto-grants-1989_06
Patent number
US04837349

Reaction notes

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