Methanol → HCID 12074218, compound

HRID 1356548Notes

Reaction equation

HRID 1356548 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][CH2:18]3)=[CH:13][C:12]=2[N+:31]([O-])=O)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.CO.[H][H]>C1COCC1.CCO.[Pd]>[NH2:31][C:12]1[CH:13]=[C:14]([N:17]2[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][CH2:18]2)[CH:15]=[CH:16][C:11]=1[S:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)(=[O:9])=[O:10]

Participants

7

Reactant 3

HCID 887MethanolHCID 12074217HCID 12074217, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 12074218HCID 12074218, compoundYield 98.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 4-{4-[(3-fluorophenyl)sulfonyl]-3-nitrophenyl}-1, 4-diazepane-1-carboxylate (58.0 g, 121 mmol) and Pd/C (8.70 g, 15% by wt.) in 1.5 L of a 2:2:1 THF:MeOH:EtOH solvent is exposed to hydrogen gas (25 psi) in a Parr bottle. The pressure of hydrogen is constantly monitored and kept near 25 psi. After 16 h, the mixture is filtered, solids rinsed with MeOH and CH2Cl2, and filtrate concentrated to give a brown solid. The solid is triturated with EtOAc and hexane to give 53.4 g (98%) of the title compound as an off white solid.

Workup

  1. filtrationthe mixture is filtered
  2. washsolids rinsed with MeOH and CH2Cl2, and filtrate
  3. concentrationconcentrated
  4. customto give a brown solid
  5. customThe solid is triturated with EtOAc and hexane

Sources & evidence

ORD record
ord-c8f3144aa5154df4937ed649517541b1
Source dataset
uspto-grants-2003_07
Patent number
US06586592B2

Reaction notes

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