HCID 22122044, compound → HCID 22121987, compound

HRID 1859361Notes

Reaction equation

HRID 1859361 reaction equation
Cl.C([O:9][NH:10][C:11](=[O:41])[CH:12]([N:16]([CH2:28][CH2:29][C:30]([N:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][OH:40])[CH2:34][CH2:33]1)=[O:31])[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH:13]([CH3:15])[CH3:14])C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:9][NH:10][C:11](=[O:41])[CH:12]([N:16]([CH2:28][CH2:29][C:30]([N:32]1[CH2:33][CH2:34][N:35]([CH2:38][CH2:39][OH:40])[CH2:36][CH2:37]1)=[O:31])[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 22122044HCID 22122044, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22121987HCID 22121987, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-benzyloxy-2-[{3-[4-(2-hydroxyethyl)piperazin-1-yl]-3-oxopropyl}-(4-methoxybenzenesulfonyl)amino]-3-methylbutyramide hydrochloride (0.39 grams, 0.63 mmol) in methanol (30 mL) was added 5% palladium on barium sulfate (0.19 grams). The mixture was agitated under 3 atmospheres hydrogen in a Parr shaker for 2.25 hours. The catalyst was removed by filtration through nylon (pore size 0.45 μm) and the solvent was evaporated to a tan foam which was chromatographed on silica gel eluting with 15% methanol in chloroform containing 0.5% ammonium hydroxide. Clean fractions containing the desired product were taken up in saturated sodium bicarbonate solution. The resulting mixture was extracted several times with ethyl acetate and the combined extracts were concentrated to afford N-hydroxy-2-[{3-[4-(2-hydroxyethyl)piperazin-1-yl]-3-oxopropyl}-(4-methoxybenzenesulfonyl)amino]-3-methyl-butyramide as an oil. The hydrochloride salt (0.20 grams, 61%) was formed using anhydrous hydrochloric acid in cold (0° C.) methanol. MS: 487 (M+1). Analysis calculated for C21H34N4O7S.circle-solid.HCl.circle-solid.0.5H2O: C, 47.41; H, 6.82; N, 10.53. Found: C, 47.41; H, 7.11; N, 9.91.

Workup

  1. customThe catalyst was removed by filtration through nylon (pore size 0.45 μm)
  2. customthe solvent was evaporated to a tan foam which
  3. customwas chromatographed on silica gel eluting with 15% methanol in chloroform containing 0.5% ammonium hydroxide
  4. additioncontaining the desired product
  5. extractionThe resulting mixture was extracted several times with ethyl acetate
  6. concentrationthe combined extracts were concentrated

Sources & evidence

ORD record
ord-e54ed64f1952416094d858a85f558545
Source dataset
uspto-grants-2000_11
Patent number
US06153609

Reaction notes

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