Tetrahydrofuran → HCID 54098096, compound

HRID 1729542Notes

Reaction equation

HRID 1729542 reaction equation
[Cl:1][CH2:2][CH:3]1[CH2:7][N:6]([C:8]([OH:10])=[O:9])[C:5]2[CH:11]=[C:12]([O:19]CC3C=CC=CC=3)[C:13]3[NH:14][CH:15]=[C:16]([CH3:18])[C:17]=3[C:4]1=2.C1COCC1.C([O-])=O.[NH4+]>[Pd].CO>[Cl:1][CH2:2][CH:3]1[CH2:7][N:6]([C:8]([OH:10])=[O:9])[C:5]2[CH:11]=[C:12]([OH:19])[C:13]3[NH:14][CH:15]=[C:16]([CH3:18])[C:17]=3[C:4]1=2

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 2723923Ammonium formateHCID 19013009HCID 19013009, compound

Product 1

HCID 54098096HCID 54098096, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 110 mg quantity (0.26 mM) of the product of Step 4A, 1,1-dimethylethyl ester of 1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid, is stirred at room temperature under nitrogen in 2 ml freshly distilled THF and 2 ml methanol. 120 mg 10% Pd/C (palladium on charcoal) and 130 mg ammonium formate is added. After TLC shows the reaction mixture to be complete, the reaction mixture is filtered, and the solid washed with freshly distilled THF. The combined filtrate and wash is partitioned between ethyl acetate and brine (saturated aqueous sodium chloride solution), the layers separated and the aqueous layer reextracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate and evaporated yield (BOC)CPI hydrochloride, 1,1-dimethylethyl ester of 1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methyl-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid.

Workup

  1. filtrationthe reaction mixture is filtered
  2. washthe solid washed with freshly distilled THF
  3. washThe combined filtrate and wash
  4. customis partitioned between ethyl acetate and brine (saturated aqueous sodium chloride solution)
  5. customthe layers separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-8353bfe9f7714079aef52fe56586074a
Source dataset
uspto-grants-1994_07
Patent number
US05332837

Reaction notes

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