Triethylamine → N-(benzyloxysuccinyl)sarcosyl-L-prolinol

HRID 467160Notes

Reaction equation

HRID 467160 reaction equation
[CH2:1]([O:8][C:9](=[O:20])[CH2:10][CH2:11][C:12]([N:14]([CH2:16][C:17]([OH:19])=O)[CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH2:27][CH2:26][CH2:25][C@H:22]1[CH2:23][OH:24].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:20])[CH2:10][CH2:11][C:12]([N:14]([CH2:16][C:17]([N:21]1[CH2:27][CH2:26][CH2:25][C@H:22]1[CH2:23][OH:24])=[O:19])[CH3:15])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 640091L-ProlinolHCID 70041319N-(benzyloxysuccinyl)sarcosine

Product 1

HCID 70043157N-(benzyloxysuccinyl)sarcosyl-L-prolinolYield 48.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(benzyloxysuccinyl)sarcosine (139.5 g, 0.5 mol), L-prolinol (50.5 g, 0.5 mol) and triethylamine (200 ml) are dissolved in methylene chloride (2 l), and a solution of DMC (127 g, 0.75 mol) in methylene chloride (500 ml) is added dropwise thereto under water-cooling over a period of thirty minutes. The mixture is stirred at room temperature for a further three hours, and the reaction liquid is washed successively with water (1 l), a saturated aqueous solution of sodium hydrogen carbonate (1 l), 1N hydrochloric acid (1 l) and water (1 l). The organic layer is dried over anhydrous magnesium sulfate and filtered. The filtrate is then concentrated to dryness under reduced pressure, and the residue is purified by column chromatography on silica gel (chloroform:methanol) to give N-(benzyloxysuccinyl)sarcosyl-L-prolinol (88.4 g, 48.8%).

Workup

  1. temperatureunder water-cooling over a period of thirty minutes
  2. customthe reaction liquid
  3. washis washed successively with water (1 l)
  4. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is then concentrated to dryness under reduced pressure
  7. customthe residue is purified by column chromatography on silica gel (chloroform:methanol)

Sources & evidence

ORD record
ord-b13725b7bcbd438a87f4ce44af46bc86
Source dataset
uspto-grants-1992_10
Patent number
US05158970

Reaction notes

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