Diisopropylethylamine → 3-[5-(2-Acetoxy-2-methyl-propionylamino)-4-carbamoyl-thiophen-2-ylsulfanyl]-propionic acid 2-ethyl-hexyl ester

HRID 1049867Notes

Reaction equation

HRID 1049867 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8](=[O:16])[C:9]([O:12][C:13](=[O:15])[CH3:14])([CH3:11])[CH3:10])=[C:4]([C:17](=[O:19])[NH2:18])[CH:3]=1.CCN(C(C)C)C(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH2:71]([CH:73]([CH2:81][CH2:82][CH2:83][CH3:84])[CH2:74][O:75][C:76](=[O:80])[CH2:77][CH2:78][SH:79])[CH3:72]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:71]([CH:73]([CH2:81][CH2:82][CH2:83][CH3:84])[CH2:74][O:75][C:76](=[O:80])[CH2:77][CH2:78][S:79][C:2]1[S:6][C:5]([NH:7][C:8](=[O:16])[C:9]([O:12][C:13](=[O:15])[CH3:14])([CH3:11])[CH3:10])=[C:4]([C:17](=[O:19])[NH2:18])[CH:3]=1)[CH3:72]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 926402-Ethylhexyl 3-mercaptopropionateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 117717729[2-[(5-Bromo-3-carbamoyl-2-thienyl)amino]-1,1-dimethyl-2-oxo-ethyl]acetate

Product 1

HCID 1177177853-[5-(2-Acetoxy-2-methyl-propionylamino)-4-carbamoyl-thiophen-2-ylsulfanyl]-propionic acid 2-ethyl-hexyl ester

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Intermediate 11 (1.4 g, 4 mmol) is dissolved in toluene (16 mL) and DIEA (1.4 mL, 8 mmol). Next, Pd2dba3 (110 mg, 0.12 mmol), Xantphos (139 mg, 0.24 mmol) and 3-Mercaptopropionic acid 2-ethylhexylester (1.14 mL, 5 mmol) are added, and the resulting solution is flushed with N2. Reaction mixture is stirred at 110° C. overnight. After evaporation, the crude is purified using column chromatography. The resulting product is obtained as an oil, which crystallised overnight. Obtained product is used as such.

Workup

  1. customthe resulting solution is flushed with N2
  2. customReaction mixture
  3. customAfter evaporation
  4. customthe crude is purified
  5. customThe resulting product is obtained as an oil, which
  6. customcrystallised overnight

Sources & evidence

ORD record
ord-c686567f3d01469b809b2228195b9e7b
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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