Potassium bisulfate → HCID 68855356, compound

HRID 1782729Notes

Reaction equation

HRID 1782729 reaction equation
C1(COC([NH:11][C@@H:12]([C:23]([NH:25][C@H:26]([C:39]([N:41]2[CH2:46][CH2:45][N:44]([C:47]3[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=3)[CH2:43][CH2:42]2)=[O:40])[CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:24])[CH2:13][C:14]2[CH:19]=[C:18]([Cl:20])[C:17]([OH:21])=[C:16]([Cl:22])[CH:15]=2)=O)C=CC=CC=1.S([O-])(O)(=O)=O.[K+].[H][H]>CO.[Pd]>[Cl:20][C:18]1[CH:19]=[C:14]([CH:15]=[C:16]([Cl:22])[C:17]=1[OH:21])[CH2:13][C@H:12]([C:23]([NH:25][C@H:26]([C:39]([N:41]1[CH2:42][CH2:43][N:44]([C:47]2[CH:52]=[CH:51][N:50]=[CH:49][CH:48]=2)[CH2:45][CH2:46]1)=[O:40])[CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:33])=[O:24])[NH2:11]

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 68854068HCID 68854068, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68855356HCID 68855356, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6 g (7.9 mmol) of 1-[N2—[N-[(phenylmethoxy)carbonyl]-3,5-dichloro-D-tyrosyl]-N6-[(1,1-dimethylethoxy)carbonyl]-L-lysyl]-4-(4-pyridinyl)-piperazine in a mixture of 200 ml of methanol and 20 ml of aqueous 1 M potassium hydrogen sulphate solution was hydrogenated in the presence of 0.5 g palladium black as catalyst at room temperature under 3 bar of hydrogen pressure for 40 minutes. The catalyst was filtered off, the reaction mixture was evaporated to dryness in vacuo and the residue adjusted to a pH of about 10 by the addition of 2 ml of concentrated aqueous ammonia solution. The product was extracted several times with isopropanol, the combined isopropanol extracts were evaporated down in vacuo and the residue was purified by column chromatography (LiChroprep, Si60 particle size: 20-40 μm, Messrs. Merck (Darmstadt); eluant: methylene chloride/methanol/ammonia=350/75/75/10 (v/v/v/v)). 2.5 g (51% of theory) of a colourless amorphous solid substance were obtained.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe reaction mixture was evaporated to dryness in vacuo
  3. additionthe residue adjusted to a pH of about 10 by the addition of 2 ml of concentrated aqueous ammonia solution
  4. extractionThe product was extracted several times with isopropanol
  5. customthe combined isopropanol extracts were evaporated down in vacuo
  6. customthe residue was purified by column chromatography (LiChroprep, Si60 particle size: 20-40 μm, Messrs. Merck (Darmstadt); eluant: methylene chloride/methanol/ammonia=350/75/75/10 (v/v/v/v))
  7. custom2.5 g (51% of theory) of a colourless amorphous solid substance were obtained

Sources & evidence

ORD record
ord-70374705afdb455697fa2afcb8e444c1
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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