HCID 15896003, compound → HCID 445018, compound

HRID 1954054Notes

Reaction equation

HRID 1954054 reaction equation
C([O:8][NH:9][C:10]([C@H:12]1[CH2:17][C:16](=[O:18])[N:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][N:13]1[S:26]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)(=[O:28])=[O:27])=[O:11])C1C=CC=CC=1>CO.[Pd]>[OH:8][NH:9][C:10]([C@H:12]1[CH2:17][C:16](=[O:18])[N:15]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:14][N:13]1[S:26]([C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)(=[O:28])=[O:27])=[O:11]

Participants

4

Reactant 1

HCID 15896003HCID 15896003, compound

Product 1

HCID 445018HCID 445018, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-Hydroxy 1-benzyl-3-[(4Methoxyphenyl)sulfonyl]-6-oxo-hexahydro-pyrimidine4(R-carboxamide (1f): A mixture of N-benzyloxy 1-benzyl-3-[(4-Methoxyphenyl)sulfonyl]-6-oxo-hexahydro-pyrimidine-4(R)-carboxamide (213 mg, 0.4 mmol) and 10% Pd/C (50 mg) in methanol (25 mL) is stirred under hydrogen atmosphere for 3 hours. The mixture is filtered over celite and the filtrate is collected and concentrated under reduced pressure to give an oil. The crude product is purified by flash silica gel chromatography (200:1 ethyl acetate-formic acid) to give N-hydroxy 1-benyl-3-[(4-methoxyphenyl)sulfonyl]-6-oxo-hexahydro-pyrimidine-4(R)-carboxamide as a white solid. MS (ESI): 420 (M+H+), 437 (M+NH4+).

Workup

  1. filtrationThe mixture is filtered over celite
  2. customthe filtrate is collected
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil
  5. customThe crude product is purified by flash silica gel chromatography (200:1 ethyl acetate-formic acid)

Sources & evidence

ORD record
ord-da60e762c4804c0892a18d8e5024afdc
Source dataset
uspto-grants-2000_09
Patent number
US06121258

Reaction notes

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