Isopropylamine → HCID 86607614, compound

HRID 2357608Notes

Reaction equation

HRID 2357608 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH:11]([CH3:12])[CH2:10][CH2:9][C@@H:8]1[C:13]([OH:15])=O)=[O:6])[CH:2]=[CH2:3].[N:16]1(O)[C:20]2[CH:21]=CC=C[C:19]=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N)(C)C>ClCCl>[CH:20]([NH:16][C:13]([C@H:8]1[CH2:9][CH2:10][CH:11]([CH3:12])[N:7]1[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[O:15])([CH3:21])[CH3:19]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68452652HCID 68452652, compound

Product 1

HCID 86607614HCID 86607614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-1-(Allyloxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid (0.92 g, 4.3 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (0.70 g, 5.2 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.0 g, 5.2 mmol), and isopropylamine (0.44 mL, 5.2 mmol) were dissolved in dichloromethane (2 mL) and stirred at ambient temperature for 16 h. The reaction was diluted with dichloromethane (100 mL), washed 3× with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotovap to give crude product. The crude was purified by chromatography to obtain the title compound. Found MS (ES+): 255(M+H)+.

Workup

  1. washwashed 3× with 50 mL of sodium bicarbonate (saturated, aqueous)
  2. customseparated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated via rotovap
  5. customto give crude product
  6. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-444e1fbdbe8d492f8c6955c18f614529
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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