1-(1,1-Dimethylethyl) hydrogen L-glutamate → HCID 87347291, compound

HRID 476352Notes

Reaction equation

HRID 476352 reaction equation
O=C1CCC(=O)N1O[C:9](=[O:35])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].[NH2:36][C@H:37]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:38][CH2:39][C:40](=[O:42])[OH:41]>C1COCC1.CN(C=O)C.O>[C:46]([O:45][C:43](=[O:44])[C@@H:37]([NH:36][C:9](=[O:35])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:38][CH2:39][C:40]([OH:42])=[O:41])([CH3:49])([CH3:47])[CH3:48]

Participants

5

Reactant 2

HCID 1175051-(1,1-Dimethylethyl) hydrogen L-glutamateHCID 58238709HCID 58238709, compound

Product 1

HCID 87347291HCID 87347291, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

Eicosanedioic acid tert-butyl ester 2,5-dioxo-pyrrolidin-1-yl ester (6.01 g, 12.124 mmol) was dissolved in THF (150 mL) and mixed with a slurry of H-Glu-OtBu (2.71 g, 13.33 mmol) in DMF/water (1/1, 40 mL). This resulted in a gel-like solution which was heated to give a clear solution that was stirred at RT for 3 h. Then the solution was evaporated, 100 mL of water was added and the mixture was heated to 60° C. which resulted in a solution which crystallised on cooling. The precipitate was recrystallised from acetonitrile and the crystals were dried in vacuum. Yield 6.82 g (96%).

Workup

  1. customThis resulted in a gel-like solution which
  2. temperaturewas heated
  3. customto give a clear solution that
  4. customThen the solution was evaporated
  5. addition100 mL of water was added
  6. temperaturethe mixture was heated to 60° C. which
  7. customresulted in a solution which
  8. customcrystallised
  9. temperatureon cooling
  10. customThe precipitate was recrystallised from acetonitrile
  11. customthe crystals were dried in vacuum

Sources & evidence

ORD record
ord-cd05ef973fd34dc7b2fd7df4485d3871
Source dataset
uspto-grants-2014_01
Patent number
US08637647B2

Reaction notes

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