Anisole → HCID 54499024, compound

HRID 236500Notes

Reaction equation

HRID 236500 reaction equation
C(OC([NH:8][C@H:9]([C:13]([NH:15][C@H:16]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:17][CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.C1(OC)C=CC=CC=1.C(N(CC)CC)C.[C:54](Cl)(=[O:62])[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61]>FC(F)(F)C(O)=O.C1C=CC=CC=1.O1CCCC1.C(Cl)(Cl)Cl>[C:54]([NH:8][C@H:9]([C:13]([NH:15][C@H:16]([C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[CH2:17][CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:14])[CH:10]([CH3:11])[CH3:12])(=[O:62])[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61]

Participants

9

Reactant 4

HCID 7519AnisoleHCID 8124Octanoyl chlorideHCID 8471TriethylamineHCID 54081958dibenzyl N-(N-tert-butoxycarbonyl-L-valyl)glutamate

Product 1

HCID 54499024HCID 54499024, compound

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of dibenzyl N-(N-tert-butoxycarbonyl-L-valyl)glutamate (1 g) and anisole (1 ml) in trifluoroacetic acid (2 ml) was stirred at 0° C. for 1 hour. Evaporation of trifluoroacetic acid under reduced pressure gave a residue which was taken up in benzene. Benzene was distilled off by using high vacuum pump. This operation was repeated three times to leave crude dibenzyl N-(L-valyl)-L-glutamate, which was dissolved in tetrahydrofuran (20 ml). To this solution was added triethylamine (1 ml) and n-octanoyl chloride (0.7 ml) at 0° C., and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with chloroform and the organic layer was washed with 1N hydrochloric acid solution, aqueous sodium carbonate solution and brine successively, dried over magnesium sulfate. After solvent was evaporated, the residue was crystallized from ethyl acetate to afford white amorphous powder of dibenzyl N-(N-octanoyl-L-valyl)-L-glutamate (600 mg).

Workup

  1. customEvaporation of trifluoroacetic acid under reduced pressure
  2. customgave a residue which
  3. distillationBenzene was distilled off
  4. customto leave crude dibenzyl N-(L-valyl)-L-glutamate, which
  5. washthe organic layer was washed with 1N hydrochloric acid solution, aqueous sodium carbonate solution and brine successively
  6. dry with materialdried over magnesium sulfate
  7. customAfter solvent was evaporated
  8. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9885459e1c7342848e2ff4a084b95869
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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