Triethylamine → HCID 54294220, compound

HRID 1647063Notes

Reaction equation

HRID 1647063 reaction equation
[C:1]1([CH:7]([O:14][C:15](=[O:40])[C@@H:16]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:17][C:18]2[CH:23]=[CH:22][C:21](OS(C(F)(F)F)(=O)=O)=[CH:20][CH:19]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:41]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])(=[O:44])[CH:42]=[CH2:43].C(N(CC)CC)C>CN(C=O)C.C(O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([CH:7]([O:14][C:15](=[O:40])[C@@H:16]([NH:32][C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH:43]=[CH:42][C:41]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[CH:22][CH:23]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 14560581HCID 14560581, compound

Product 1

HCID 54294220HCID 54294220, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Bis(triphenylphosphine) palladium dichloride (120 mg, 0.2 mmol) was added to a deoxygenated mixture of (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[4-[[(trifluoromethyl)sulfonyl]oxy]phenyl]propanoic acid diphenylmethyl ester (3.0 g, 5.2 mmol), t-butyl acrylate (1.5 mL, 10.2 mmol) and triethylamine (4.0 mL, 30.0 mmol) in DMF (50 mL) and the well-stirred suspension was then heated at 90° C. (24 h). The solvent was removed in vacuo and the resulting residue was purified by flash chromatography on silica gel eluting with a mixture of dichloromethane and hexanes (8:1) to give the (S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-3-[4-[3-(1,1-dimethylethoxy)-3-oxo-1-propenyl]phenyl]propanoic acid diphenylmethyl ester (1.6 g, 2.8 mmol) in 54% yield, mp. 135°-137° C., [α]D -5.35° (0.97 % in ethanol).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was purified by flash chromatography on silica gel eluting with a mixture of dichloromethane and hexanes (8:1)

Sources & evidence

ORD record
ord-61f080c84e9249fe887e9aea486fdc07
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

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