Dicyclohexylcarbodiimide → (S)-tert-butyl 1-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethylcarbamate

HRID 57390Notes

Reaction equation

HRID 57390 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[N:8][OH:9])[NH2:7])=[CH:4][CH:3]=1.[C:12]([O:16][C:17]([NH:19][C@@H:20]([CH3:24])[C:21](O)=O)=[O:18])([CH3:15])([CH3:14])[CH3:13].C1CCC(N=C=NC2CCCCC2)CC1>O1CCOCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:7]=[C:24]([C@@H:20]([NH:19][C:17](=[O:18])[O:16][C:12]([CH3:13])([CH3:15])[CH3:14])[CH3:21])[O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 2246504-chloro-N'-hydroxybenzenecarboximidamide

Product 1

HCID 90414461(S)-tert-butyl 1-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethylcarbamateYield 48%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-chloro-N′-hydroxybenzimidamide (1.24 g, 7.27 mmol), (S)-2-(tert-butoxycarbonylamino)propanoic acid (1.38 g, 7.27 mmol, 1.0 equiv), and DCC (1.65 g, 8.00 mmol, 1.1 equiv) in 1,4-dioxane (73 mL) was heated at 100° C. for 18 hours. The reaction was then cooled to room temperature and concentrated in vacuo. Silica gel column chromatography (EtOAc/Heptane, 0 to 35%) provided (S)-tert-butyl 1-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)ethylcarbamate (1.13 g, white solid) in 48% yield. 1H NMR (400 MHz, CDCl3) δ 8.03 (d, J=8.8 Hz, 2H), 7.47 (d, J=8.8 Hz, 2H), 5.18 (m, 1H), 1.64 (d, J=6.8 Hz, 3H), 1.47 (s, 9H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3f5ba6193aa4df5b32f016183bb543e
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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