Triethylamine → HCID 58654405, compound

HRID 1170527Notes

Reaction equation

HRID 1170527 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH2:29]1[O:40][C:39]2[CH:38]=[CH:37][C:33]([CH2:34][CH2:35][NH2:36])=[CH:32][C:31]=2[O:30]1.C(N(CC)CC)C>ClCCCl>[C:12]([O:11][C:9](=[O:10])[NH:1][C@@H:2]([C:6](=[O:8])[NH:36][CH2:35][CH2:34][C:33]1[CH:37]=[CH:38][C:39]2[O:40][CH2:29][O:30][C:31]=2[CH:32]=1)[CH:3]([CH3:4])[CH3:5])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 742461,3-Benzodioxole-5-ethanamine, hydrochloride (1:1)HCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acid

Product 1

HCID 58654405HCID 58654405, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Boc-D-Val-OH (282 mg, 1.30 mmol) was dissolved in DCE (5 mL), followed by addition of CDI (253 mg, 1.56 mmol). The reaction solution was stirred for 30 mins to activate the acid. After this period, 3,4-Methylenedioxyphenethylamine HCl (263 mg, 1.30 mmol) and triethylamine (363 μL) were added to the reaction vessel and it was stirred at room temperature for 16 hours. Next, the reaction mixture was concentrated under vacuum. The crude material was dissolved in DCM (50 mL), transferred to a separatory funnel, washed with sat. NaHCO3 (aq) (50 mL), dried over Na2SO4 and concentrated down to yield 447.1 mg (94.6%) of crude product, [1-(2-benzo[1,3]dioxol-5-yl-ethylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester, which was taken on crude. [M+H]+ 365.00.

Workup

  1. waitAfter this period
  2. stirringwas stirred at room temperature for 16 hours
  3. concentrationNext, the reaction mixture was concentrated under vacuum
  4. dissolutionThe crude material was dissolved in DCM (50 mL)
  5. customtransferred to a separatory funnel
  6. washwashed with sat. NaHCO3 (aq) (50 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated down

Sources & evidence

ORD record
ord-fcf10e25d0c24e1d88e1ce570049552e
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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