Triethylamine → HCID 59625362, compound

HRID 2192861Notes

Reaction equation

HRID 2192861 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([C:35](O)=[O:36])[N:11]([C:16]([C:18]1[C:19]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[N:20][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[N:22][CH:23]=1)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:38]1(O)C2C=CC=CC=2N=N1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>ClCCCl.CN(C=O)C>[NH2:38][C:35](=[O:36])[C@@H:10]([N:11]([C:16]([C:18]1[C:19]([NH:28][CH2:29][C:30]2[O:31][CH:32]=[CH:33][CH:34]=2)=[N:20][C:21]([C:24]([CH3:26])([CH3:27])[CH3:25])=[N:22][CH:23]=1)=[O:17])[CH2:12][CH:13]([CH3:14])[CH3:15])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59625450HCID 59625450, compound

Product 1

HCID 59625362HCID 59625362, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 20184825Dce dmfSolvent

Procedure

3-[(tert-Butoxycarbonyl)amino]-N-({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)-N-(2-methylpropyl)-L-alanine (147 mg), 1H-1,2,3-benzotriazol-1-ol ammoniate (130 mg) and triethylamine (160 μl) were dissolved in 1,2-dichloroethane-DMF (3:1, 15 ml), WSC.HCl (163 mg) was added and the mixture was stirred at room temperature for 21 hr. The reaction mixture was concentrated under reduced pressure, and diluted with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (1:9) to ethyl acetate was concentrated under reduced pressure to give the object compound (90 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with saturated aqueous sodium hydrogen carbonate
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washthe fraction eluted with ethyl acetate-hexane (1:9) to ethyl acetate
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-37b35170e4c146e4848adf0fd736bed0
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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