Tert-butyl N2-(((9H-fluoren-9-YL)methoxy)carbonyl)-N5,N5-dimethyl-L-glutaminate → (2S)-4-(dimethylcarbamoyl)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid

HRID 1482235Notes

Reaction equation

HRID 1482235 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]([N:31]([CH3:33])[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]([N:31]([CH3:33])[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 89668280Tert-butyl N2-(((9H-fluoren-9-YL)methoxy)carbonyl)-N5,N5-dimethyl-L-glutaminate

Product 1

HCID 89668277(2S)-4-(dimethylcarbamoyl)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(dimethylamino)-5-oxopentanoate (Compound SP447) (15.2 g, crude product) was dissolved in a mixture of dichloromethane (200 ml) and trifluoroacetic acid (200 ml), followed by stirring at room temperature for 2.5 hours. The solvent was evaporated under reduced pressure, and the resulting solid was washed with a mixed solution of hexane and tert-butyl methyl ether and then dried in vacuo to afford (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(dimethylamino)-5-oxopentanoic acid (Compound SP448) (9.12 g, 85%, two steps).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe resulting solid was washed with a mixed solution of hexane and tert-butyl methyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-3c9d970dacf24ad99062f2a8e4e266b1
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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