Benzyl azide → (S)-3-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid

HRID 1185571Notes

Reaction equation

HRID 1185571 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH2:10][C:11]#[CH:12])=[O:7])([CH3:4])[CH3:3].[CH2:16]([N:23]=[N+:24]=[N-:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O.CC(O)(C)C.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:16]([N:23]1[CH:12]=[C:11]([CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:13]([OH:15])=[O:14])[N:25]=[N:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 12152Benzyl azideHCID 2734488(2S)-2-{[(tert-butoxy)carbonyl]amino}pent-4-ynoic acidHCID 23667548Sodium Ascorbate

Product 1

HCID 68599866(S)-3-(1-Benzyl-1H-[1,2,3]triazol-4-yl)-2-tert-butoxycarbonylamino-propionic acid

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 8857Ethyl AcetateSolventHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

A mixture of 430 mg Boc-L-propargylglycine, 269 mg benzyl azide, 36 mg copper(II)acetate and 80 mg sodium ascorbate in 15 ml water/t-BuOH (1:1) was stirred for 12 h at RT. The reaction mixture was diluted with ethyl acetate, washed with brine (2×) and the aqueous phase reextracted with ethyl acetate. The crude product obtained after evaporation of the solvent was pure enough for the subsequent transformation. Yield: 855 mg.

Workup

  1. washwashed with brine (2×)

Sources & evidence

ORD record
ord-dff70ad1aa5a4e628f13b9d28dfbcbba
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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