HCID 86705343, compound → HCID 86705342, compound

HRID 587988Notes

Reaction equation

HRID 587988 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([O:15][C:16](=[O:41])[C:17]([CH2:39][CH3:40])([CH2:37][CH3:38])[CH2:18][C:19]1[S:20][C:21]([C:24]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33](=[NH:35])[NH2:34])=[CH:29][C:28]=2[F:36])=[O:25])=[CH:22][CH:23]=1)C1C=CC=CC=1>CC(O)C.O.[OH-].[Pd+2].[OH-]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:33]([C:30]1[CH:31]=[CH:32][C:27]([O:26][C:24]([C:21]2[S:20][C:19]([CH2:18][C:17]([CH2:39][CH3:40])([CH2:37][CH3:38])[C:16]([OH:41])=[O:15])=[CH:23][CH:22]=2)=[O:25])=[C:28]([F:36])[CH:29]=1)(=[NH:34])[NH2:35]

Participants

5

Reactant 1

HCID 86705343HCID 86705343, compound

Product 1

HCID 86705342HCID 86705342, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

3-[5-(4-Amidino-2-fluorophenoxycarbonyl)thiophen-2-yl]-2,2-diethylpropanoic acid benzyl ester trifluoroacetic acid salt (4.3 g, 7.21 mmol) was dissolved in 2-propanol (160 mL) and water (40 mL), palladium hydroxide (0.9 g) was added, and the mixture was stirred at room temperature overnight under a hydrogen atmosphere. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. Water and acetonitrile was added to the residue, the mixture was lyophilized to give the title compound (3.61 g, 7.12 mmol, 99%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater and acetonitrile was added to the residue

Sources & evidence

ORD record
ord-acde3d8299c840e48112163ad02560fe
Source dataset
uspto-grants-2016_01
Patent number
US09227949B2

Reaction notes

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