Methane → HCID 86757700, compound

HRID 1249707Notes

Reaction equation

HRID 1249707 reaction equation
[NH2:1][C:2](=[N:37]O)[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([NH:18][CH2:19][C@H:20]([NH:26][S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:17])[C:11](=[O:36])[CH2:10]2)=[CH:5][CH:4]=1.C(OC(=O)C)(=O)C.C>C(O)(=O)C.O.[Pd]>[C:21]([OH:23])(=[O:22])[CH3:20].[NH2:37][C:2](=[NH:1])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([NH:18][CH2:19][C@H:20]([NH:26][S:27]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)(=[O:29])=[O:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:17])[C:11](=[O:36])[CH2:10]2)=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 297MethaneHCID 7918Acetic AnhydrideHCID 86757702HCID 86757702, compound

Product 1

HCID 86757700HCID 86757700, compoundYield 160.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Ethyl (2S) -3-{[2- (4-{4-[amino(hydroxyimino)methyl]phenyl}-2-oxopiperazino)acetyl]amino}-2-[(phenylsulphonyl)amino]propanoate (Example 1) (1.5 g, 2.75 mmol) is dissolved in 50 ml of acetic acid. 600 mg of acetic anhydride (5.6 mmol) and 0.76 g of 10%; palladium-on-charcoal are added. The hydrogenolysis is carried out at room temperature under 50 psi for 3 hours. The catalyst is filtered off and the solution is evaporated to dryness. The solid obtained is dissolved in 150 ml of water and treated with charcoal. The solution is filtered. The filtrate is freeze-dried to give 1.3 g of a white solid.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solution is evaporated to dryness
  3. customThe solid obtained
  4. filtrationThe solution is filtered
  5. customThe filtrate is freeze-dried

Sources & evidence

ORD record
ord-7d8fb2150b52417fa25299fa356e29f1
Source dataset
uspto-grants-2002_01
Patent number
US06335337B1

Reaction notes

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