Nepsilon-(4-nitrobenzenesulfonyl)-Nalpha-(9-fluorenylmethoxycarbonyl)-L-lysine → Nepsilon-(4-aminobenzenesulfonyl)-Nalpha-(9-fluorenylmethoxycarbonyl)-L-lysine

HRID 1282484Notes

Reaction equation

HRID 1282484 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][C@@H:18]([C:37]([OH:39])=[O:38])[NH:19][C:20]([O:22][CH2:23][CH:24]2[C:36]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:30]3[C:25]2=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][C@@H:18]([C:37]([OH:39])=[O:38])[NH:19][C:20]([O:22][CH2:23][CH:24]2[C:36]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[C:30]3[C:25]2=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])(=[O:11])=[O:12])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 14258337Nepsilon-(4-nitrobenzenesulfonyl)-Nalpha-(9-fluorenylmethoxycarbonyl)-L-lysine

Product 1

HCID 86604312Nepsilon-(4-aminobenzenesulfonyl)-Nalpha-(9-fluorenylmethoxycarbonyl)-L-lysineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The product obtained from example 3 (553 mg, 1.00 mmol) was dissolved in EtOAc (10 mL) and then hydrogenated using 10% Pd on charcoal as catalyst at atmospheric pressure for 2 h. The catalyst was filtered off and the filtrate was evaporated in vacuo to yield the title compound in 95% yield.

Workup

  1. customfor 2 h
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-f88801d25e0443e48ba01b98671a034e
Source dataset
uspto-grants-2002_09
Patent number
US06455587B1

Reaction notes

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