Hydrochloric Acid → HCID 10041457, compound

HRID 1590965Notes

Reaction equation

HRID 1590965 reaction equation
CCN=C=NCCCN(C)C.[NH:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:13]([C:18]([OH:20])=O)[CH2:14][CH:15]([CH3:17])[CH3:16].O.Cl.[NH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].C1C=CC2N(O)N=NC=2C=1>ClCCl>[NH:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:13]([C:18]([NH:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:20])[CH2:14][CH:15]([CH3:16])[CH3:17]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 12176Glycine ethyl esterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 10041457HCID 10041457, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.10 Milliliters of WSC was gradually added to 100 ml of a solution of 12.47 g of Boc-Leu-OH.H2O, 6.98 g of HCl.H-Gly-OEt and 6.76 g of HOBT dissolved in dichloromethane, with ice-cooling. The mixture was stirred for 42 hours at room temperature. The reaction mixture was mixed with 100 ml of 1N hydrochloric acid, and the resulting precipitate was removed by filtration. The filtrate was washed with 100 ml of 1N hydrochloric acid, two 100-ml portions of a saturated aqueous sodium bicarbonate solution and 100 ml of a saturated aqueous sodium chloride solution in this order, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue was added petroleum ether to crystallize the residue. The resulting crystal was recrystallized from ethyl acetate-petroleum ether to obtain 8.68 g (yield: 56.6%) of the above objective compound. Melting point: 79.5°-82.5° C.

Workup

  1. temperaturecooling
  2. customthe resulting precipitate was removed by filtration
  3. washThe filtrate was washed with 100 ml of 1N hydrochloric acid, two 100-ml portions of a saturated aqueous sodium bicarbonate solution and 100 ml of a saturated aqueous sodium chloride solution in this order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added petroleum ether
  7. customto crystallize the residue
  8. customThe resulting crystal was recrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-1c1c04aba03843888c9e86c9df1df548
Source dataset
uspto-grants-1993_04
Patent number
US05204326

Reaction notes

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