Triethylamine → HCID 58124406, compound

HRID 1965892Notes

Reaction equation

HRID 1965892 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:3]([CH3:6])([CH3:5])[CH3:4].[NH2:17][CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].Cl.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([NH:17][CH2:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:9])[C:3]([CH3:4])([CH3:5])[CH3:6]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acidHCID 11701227Benzyl 2-aminoacetate hydrochloride

Product 1

HCID 58124406HCID 58124406, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Boc-t-Leu-OH (9.26 g, 40.0 mmol) and Gly-OBzl•HCl (8.06 g, 40.0 mmol) were dissolved in methylene chloride (60 ml), and the solution was maintained at 0° C. Triethylamine (5.60 ml, 40.0 mmol), HOBt (1-hydroxybenzotriazole, 6.75 g, 44.0 mmol), and WSC•HCl (1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, 8.47 g, 44.0 mmol) were added to the solution, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (200 ml). The solution was washed with water (50 ml), 5% citric acid aqueous solution (50 ml, twice), saturated brine (50 ml), 5% sodium hydrogencarbonate aqueous solution (50 ml, twice), and saturated brine (50 ml). The organic layer was dried over anhydrous magnesium sulfate, then the magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-n-hexane to obtain a viscous oily material of Boc-t-Leu-Gly-OBzl (15.20 g, 40.1 mmol).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (200 ml)
  3. washThe solution was washed with water (50 ml), 5% citric acid aqueous solution (50 ml
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe magnesium sulfate was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-d69b1fe756d9490d9880719bf5afd2a7
Source dataset
uspto-grants-2013_04
Patent number
US08420144B2

Reaction notes

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