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

HRID 591344Notes

Reaction equation

HRID 591344 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].[CH3:29][S:30]([O:33][CH2:34][CH2:35][N:36]=[N+:37]=[N-:38])(=[O:32])=[O: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:38]=[N:37][N:36]([CH2:35][CH2:34][O:33][S:30]([CH3:29])(=[O:32])=[O:31])[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 112751972-Azidoethyl methanesulfonateHCID 117812721di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-prop-2-yn-1-yl-L-glutamate

Product 1

HCID 117812724di-tert-butyl (4R)-N-(tert-butoxycarbonyl)-4-[(1-{2-[(methylsulfonyl)oxy]ethyl}-1H-1,2,3-triazol-4-yl)methyl]-L-glutamateYield 58.8%

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 (60 mg, 151 μmol) and 2-azidoethyl methanesulfonate (37.4 mg, 226 μmol) were dissolved in tetrahydrofuran (4 ml). To the solution, copper(I) iodide (2.9 mg, 15 μmol) and N,N-diisopropylethylamine (32 μl, 181 μmol) were added and the mixture was stirred for 18 h at room temperature. The mixture was then concentrated in vacuo and the residue was purified by preparative reversed phase HPLC. The product fractions were collected, lyophilized, and purified again by silicagel chromatography to yield 50 mg (47%) of the product.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue was purified by preparative reversed phase HPLC
  3. customThe product fractions were collected
  4. custompurified again by silicagel chromatography

Sources & evidence

ORD record
ord-4072581f9dd8432fb91e958d3652e0f9
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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