Dimethylformamide → methyl N-{[4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexyl]carbonyl}-L-norleucinate

HRID 488655Notes

Reaction equation

HRID 488655 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=O)[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=[N:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N([OH:53])N=NC=2C=1.C(N(CC)CC)C.CN([CH:64]=[O:65])C>O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH:13]1[CH2:14][CH2:15][CH:16]([C:19]([NH:37][C@H:32]([C:31]([O:65][CH3:64])=[O:53])[CH2:33][CH2:34][CH2:35][CH3:36])=[O:21])[CH2:17][CH2:18]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 3723035Cbz-trans-4-(aminomethyl)cyclohexanecarboxylic acid

Product 1

HCID 69803360methyl N-{[4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexyl]carbonyl}-L-norleucinateYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring mixture of 4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexanecarboxylic acid (750 mg, 2.57 mmol), TBTU (1.08 g, 3.34 mmol), and HOBT (55 mg, 0.03 mmol) in DMF (15 mL) was added the norleucine OMe HCl (411 mg, 2.83 mmol), followed by addition of triethylamine (898 μL, 6.43 mmol). The resulting mixture was then stirred at ambient temperature for 2 hours, diluted with water and the resulting precipitate was collected by filtration and dried in a vacuum oven to provide the titled compound (830 mg, 1.98 mmol, 77%).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d3e4ea6171f64419853ca8606e5dd651
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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