HCID 22885749, compound → HCID 22885736, compound

HRID 1289963Notes

Reaction equation

HRID 1289963 reaction equation
COC1C=CC([CH2:7][N:8]([C@H:19]2[CH2:23][CH2:22][C@H:21]([N:24](C(OC)=O)C)[C@H:20]2[C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:9]([O:11][CH2:12]C2C=CC=CC=2)=[O:10])=CC=1>CO.[Pd]>[NH2:24][C@H:21]1[CH2:22][CH2:23][C@H:19]([N:8]([C:9]([O:11][CH3:12])=[O:10])[CH3:7])[C@H:20]1[C:30]1[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=1

Participants

4

Reactant 1

HCID 22885749HCID 22885749, compound

Product 1

HCID 22885736HCID 22885736, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the product from Step C in 10 mL of methanol was hydrogenated over 200 mg of 10% Pd/C at 40 psi for 3 days to remove first the CBz and then the PMB group. The reaction was filtered and evaporated to give 550 mg of title compound. T.l.c. (5% Methanol in methylene chloride) Rf =0.5 (PMB intermediate) and 0.2 (amine product).

Workup

  1. customto remove first the CBz
  2. filtrationThe reaction was filtered
  3. customevaporated

Sources & evidence

ORD record
ord-1b6f4634b5b944a59fd8bf459c4e18d9
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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