Triethylamine → di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[1-(2-fluoroethyl)-1H-1,2,3-triazol-4-yl]methyl}-L-glutamate

HRID 591343Notes

Reaction equation

HRID 591343 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:10][C@H:11]([CH2:19][C:20]1[N:21]=[N:22][N:23]([CH2:25][CH2:26]O)[CH:24]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:42]C(F)(C(F)(F)F)C(F)(F)C(F)(F)S(F)(=O)=O.F.F.F.C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:10][C@H:11]([CH2:19][C:20]1[N:21]=[N:22][N:23]([CH2:25][CH2:26][F:42])[CH:24]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 117812722di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]methyl}-L-glutamate

Product 1

HCID 117812673di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[1-(2-fluoroethyl)-1H-1,2,3-triazol-4-yl]methyl}-L-glutamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-{[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]methyl}-L-glutamate (74 mg, 152.7 μmol) was dissolved in tetrahydrofuran (5 ml) and triethyl amine (319 μl, 2.3 mmol), Nonafluorobutanesulfonyl fluoride (185 mg, 611 μmol), and Triethylamine trihydrofluoride (98 mg, 611 mmol) were added subsequently. The mixture was stirred at room temperature for 6 days. The mixture was than concentrated in vacuo, and the residue was purified by silica gel chromatography to yield 30 mg (40%) of slightly impure product, which was used in the following step.

Workup

  1. concentrationthan concentrated in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. customto yield 30 mg (40%) of slightly impure product, which

Sources & evidence

ORD record
ord-cd1141b71fa146afa79ebb0b93ce594e
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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