Triethylamine → HCID 131715956, compound

HRID 1904450Notes

Reaction equation

HRID 1904450 reaction equation
C(N(CC)CC)C.[C:8]([SiH:12]([CH3:14])[CH3:13])([CH3:11])([CH3:10])[CH3:9].C[O:16][C:17](=[O:29])[CH2:18][NH:19][CH2:20][CH:21]=[CH:22][C:23]([O:25]CC=C)=[O:24].[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[Si:12]([O:25][C:23]([CH:22]=[CH:21][CH2:20][NH:19][CH2:18][C:17]([OH:29])=[O:16])=[O:24])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 5072427tert-ButyldimethylsilaneHCID 131715957HCID 131715957, compound

Product 1

HCID 131715956HCID 131715956, compound

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 (16 μl, 0.12 mmol), t-butyldimethylsilane (187 μl, 1.1 mmol) was added and the mixture was stirred for 15 minutes at room temperature in an argon atmosphere. To the resulting black suspension, a dichloromethane solution (1.0 ml) of N-allyloxycarbonylallylglycine methyl ester (150 mg, 0.75 mmol) was added and the mixture was stirred for an additional 20 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-butyldimethylsilyloxycarbonylallylglycine was obtained in an amount of 184 mg (yield, 90%). The physical data for this compound were in agreement with those reported in Examples 3 and 11.

Workup

  1. stirringthe mixture was stirred for an additional 20 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-87b0aa67792b46f3a2b4ccf5093cb6ee
Source dataset
uspto-grants-1989_06
Patent number
US04837349

Reaction notes

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