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

HRID 591342Notes

Reaction equation

HRID 591342 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10][C@H:11]([CH2:19][C:20]#[CH:21])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:29]([CH2:32][CH2:33][OH:34])=[N+:30]=[N-:31].C(N(CC)C(C)C)(C)C>O1CCCC1.[Cu]I>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10][C@H:11]([CH2:19][C:20]1[N:31]=[N:30][N:29]([CH2:32][CH2:33][OH:34])[CH:21]=1)[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1231182-AzidoethanolHCID 117812721di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-prop-2-yn-1-yl-L-glutamate

Product 1

HCID 117812722di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-{[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]methyl}-L-glutamateYield 34%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-prop-2-yn-1-yl-L-glutamate (150 mg, 377 μmol) and 2-azidoethanol (49 mg, 566 μmol) were dissolved in tetrahydrofuran (3.75 ml). To the solution, copper(I) iodide (7.2 mg, 38 μmol) and N,N-diisopropylethylamine (79 μl, 453 μmol) were added and the mixture was stirred for 12 h at room temperature. The mixture was then concentrated in vacuo and the residue was purified by preparative reversed phase HPLC to yield 62 mg (34%) of the product.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue was purified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-60b35008299b44c9a9b679ff9c7f8053
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

Loading…