Triethylamine → HCID 20610310, compound

HRID 433838Notes

Reaction equation

HRID 433838 reaction equation
O.OC1C2N=NNC=2C=CC=1.[C:12]([O:16][C:17]([NH:19][C@H:20]([C:25]([OH:27])=O)[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])([CH3:15])([CH3:14])[CH3:13].[NH2:28][C:29]1[CH:30]=[C:31]([CH:36]=[CH:37][C:38]=1[NH2:39])[C:32]([O:34][CH3:35])=[O:33].C(N(CC)CC)C>CN(C)C=O.O>[CH3:35][O:34][C:32](=[O:33])[C:31]1[CH:36]=[CH:37][C:38]([NH2:39])=[C:29]([NH:28][C:25](=[O:27])[CH:20]([NH:19][C:17]([O:16][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:18])[CH2:21][CH:22]([CH3:23])[CH3:24])[CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 1355243,5-Diamino-2-methylbenzoic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 20610310HCID 20610310, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Hydroxybenzotriazole monohydrate (760 mg, 5.62 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimde hydrochloride (973 mg, 5.07 mmol) were added to a dimethyl formamide (30 mL) solution of N-tert-butoxycarbonyl-L-leucine (1.06 g, 4.57 mmol). The mixture was stirred until all 1-(3-dimethylaminopropyl)-3-ethylcarbodiimde hydrochloride had dissolved. Methyl 3,4-diaminobenzoate (759 mg, 4.57 mmol) in dimethyl formamide (10 mL) and triethyl amine (0.68 mL, 4.89 mmol) were added sequentially. The reaction was stirred at room temperature over night and poured into water. This mixture was extracted with ethyl acetate three times. The organic portion was extracted with a saturated solution of sodium bicarbonate, water (2×) and brine. The organic portion was dried over magnesium sulfate and the solvent removed in vacuo. The resulting residue was chromatographed on a Biotage Flash 40S column eluting with ethyl acetate/hexanes (2:3) which yielded the title compound (690 mg, 40%). MS (CI) m/z 380.0 (M+1), 378.2 (M−1).

Workup

  1. dissolutionhad dissolved
  2. extractionThis mixture was extracted with ethyl acetate three times
  3. extractionThe organic portion was extracted with a saturated solution of sodium bicarbonate, water (2×) and brine
  4. dry with materialThe organic portion was dried over magnesium sulfate
  5. customthe solvent removed in vacuo
  6. customThe resulting residue was chromatographed on a Biotage Flash 40S column
  7. washeluting with ethyl acetate/hexanes (2:3) which

Sources & evidence

ORD record
ord-6c7d82fda21e4759adbddd3fdbbaea64
Source dataset
uspto-grants-2003_12
Patent number
US06668527B2

Reaction notes

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