1,1'-Carbonyldiimidazole → HCID 58654458, compound

HRID 1170482Notes

Reaction equation

HRID 1170482 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([OH:6])=O)[CH3:3].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH2:27]1[O:38][C:37]2[CH:36]=[CH:35][C:31]([CH2:32][CH2:33][NH2:34])=[CH:30][C:29]=2[O:28]1>ClCCCl>[C:10]([O:9][C:7](=[O:8])[NH:1][C@H:2]([C:4](=[O:6])[NH:34][CH2:33][CH2:32][C:31]1[CH:35]=[CH:36][C:37]2[O:38][CH2:27][O:28][C:29]=2[CH:30]=1)[CH3:3])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 74246Phenethylamine, 3,4-methylenedioxy-, hydrochlorideHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 58654458HCID 58654458, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Boc-Ala-OH (222 mg, 1.20 mmol) was dissolved in DCE (4 mL), followed by addition of CDI (209 mg, 1.20 mmol). The mixture was stirred at room temperature for 30 min. 3,4-Methylenedioxyphenethylamine hydrochloride (240 mg, 1.20 mmol) and TEA (2.4 mmol) were added and the reaction was stirred at room temperature under Nitrogen for 16 hours. Next, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in DCM and transferred to a separatory funnel and washed with saturated NaHCO3 (aq). The organic layer was dried with Na2SO4 and concentrated down. The crude material was purified by flash chromatography (DCM to 9:1 DCM/MeOH) to yield 350 mg (88%) of (S)—[1-(2-benzo[1,3]dioxol-5-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester. [M+H]+ 337.05.

Workup

  1. stirringthe reaction was stirred at room temperature under Nitrogen for 16 hours
  2. concentrationNext, the reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in DCM
  4. customtransferred to a separatory funnel
  5. washwashed with saturated NaHCO3 (aq)
  6. dry with materialThe organic layer was dried with Na2SO4
  7. concentrationconcentrated down
  8. customThe crude material was purified by flash chromatography (DCM to 9:1 DCM/MeOH)

Sources & evidence

ORD record
ord-28a601f3a0b04e98970fade185aba9b2
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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