1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (s)-Tert-butyl 4-(tert-butoxycarbonylamino)-5-(2-carbamoyl-1h-pyrrol-1-ylamino)-5-oxopentanoate

HRID 218308Notes

Reaction equation

HRID 218308 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH2:9])=[O:8].[C:10]([O:14][C:15](=[O:30])[CH2:16][CH2:17][C@H:18]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:19](O)=[O:20])([CH3:13])([CH3:12])[CH3:11].Cl.CN(C)CCCN=C=NCC>C1COCC1>[C:26]([O:25][C:23]([NH:22][C@H:18]([C:19]([NH:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:8])[NH2:9])=[O:20])[CH2:17][CH2:16][C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:30])=[O:24])([CH3:28])([CH3:27])[CH3:29]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6993432(2S)-5-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acidHCID 104191801-Amino-1H-pyrrole-2-carboxamide

Product 1

HCID 59313696(s)-Tert-butyl 4-(tert-butoxycarbonylamino)-5-(2-carbamoyl-1h-pyrrol-1-ylamino)-5-oxopentanoateYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-amino-1H-pyrrole-2-carboxamide (1.00 g, 7.99 mmol) and (5)-5-tert-butoxy-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid (2.91 g, 9.59 mmol) was dissolved in THF (80 mL). To this solution was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.84 g, 9.59 mmol). The reaction was stirred at rt for 1.5 h, then concentrated in vacuo. CH2Cl2 (150 mL) was added, and the reaction mixture was washed with water (2×150 mL). The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The compound was purified by silica gel flash chromatography (0-35% 90:10:1 [CH2Cl2/MeOH/conc NH4OH]/CH2Cl2) to give 10A (2.90 g, 85%). 10A had an analytical HPLC retention time=2.05 min (Waters XBridge 4.6×50 mm, 5-95% aqueous acetonitrile over 5 min containing 10 mM ammonium acetate) and a LC/MS M−−1=409.

Workup

  1. concentrationconcentrated in vacuo
  2. additionCH2Cl2 (150 mL) was added
  3. washthe reaction mixture was washed with water (2×150 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe compound was purified by silica gel flash chromatography (0-35% 90:10:1 [CH2Cl2/MeOH/conc NH4OH]/CH2Cl2)

Sources & evidence

ORD record
ord-be6d40c4fbb0499d8687bc0569e704de
Source dataset
uspto-grants-2012_06
Patent number
US08198438B2

Reaction notes

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