Isobutylamine → Boc-Ile-NH-CH2-CH(CH3)2

HRID 2269626Notes

Reaction equation

HRID 2269626 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[C@H:3]([CH2:5][CH3:6])[CH3:4].[CH2:17]([NH2:21])[CH:18]([CH3:20])[CH3:19].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([NH:21][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:9])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724762tert-Butoxycarbonyl-L-isoleucine

Product 1

HCID 131722955Boc-Ile-NH-CH2-CH(CH3)2

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a DMF solution containing 2.0 g of Boc-Ile-OH, 0.82 ml of isobutylamine, 1.27 g of HOBt and 2.06 g of DCC were added under ice cooling and the resultant mixture was stirred for 14 hr. The reaction mixture, after filtration, was treated similarly to that in Example 50 (Process 2),except for the crystallization solvent (hexane) to give 1.44 g of the title compound.

Workup

  1. additionwere added under ice cooling
  2. filtrationThe reaction mixture, after filtration
  3. additionwas treated similarly to that in Example 50 (Process 2),except for the crystallization solvent (hexane)

Sources & evidence

ORD record
ord-803f05082126404687502064dabc1cbf
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

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