HCID 89668278, compound → N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-glutamine

HRID 1482233Notes

Reaction equation

HRID 1482233 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:27][CH2:28][C:29]([NH:31][CH3:32])=[O:30])[C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>ClCCl.FC(F)(F)C(O)=O>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:27][CH2:28][C:29]([NH:31][CH3:32])=[O:30])[C:20]([OH:22])=[O:21])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 89668278HCID 89668278, compound

Product 1

HCID 89668279N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-glutamineYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(methylamino)-5-oxopentanoate (Compound SP445) (13.3 g, crude product) was dissolved in a mixture of dichloromethane (140 ml) and trifluoroacetic acid (140 ml), followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and the resulting solid was washed with hexane and then dried in vacuo to afford (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(methylamino)-5-oxopentanoic acid (Compound SP446) (5.84 g, 93%, two steps).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe resulting solid was washed with hexane
  3. customdried in vacuo

Sources & evidence

ORD record
ord-241e68c91d41453dbeafdd47119c5317
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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