Dicyclohexylcarbodiimide → N-Benzyloxy-t-butoxycarbonyl-threonine amide

HRID 279808Notes

Reaction equation

HRID 279808 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[C@@H:10]([CH3:12])[OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:17]([O:24][NH2:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:17]([O:24][NH:25][C:13](=[O:15])[C@H:9]([C@@H:10]([CH3:12])[OH:11])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 2724766N-tert-Butoxycarbonyl-L-threonine

Product 1

HCID 18598709N-Benzyloxy-t-butoxycarbonyl-threonine amideYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8.76 g of t-butoxycarbonyl threonine and the free amine from 6.4 g of O-benzylhydroxylamine HCl (ethyl acetate-sodium bicarbonate liberation) in 100 ml of tetrahydrofuran was treated with 6.12 g of N-hydroxybenzotriazole and 8.24 g of dicyclohexylcarbodiimide in 20 ml of tetrahydrofuran. The mixture was stirred under nitrogen for 26 hours, filtered, and evaporated in vacuo. The residue was chromatographed on a 300 g silica gel column (elution with chloroform and chloroform/ethyl acetate (3:1) yielding 7.2 g of compound. Crystallization from ether-hexane gave 4.18 g of the title compound.

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo
  3. customThe residue was chromatographed on a 300 g silica gel column (
  4. washelution with chloroform and chloroform/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-1b7b103fc8964cb89547ebb1b559d792
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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