Triethylamine → HCID 70041852, compound

HRID 467159Notes

Reaction equation

HRID 467159 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[CH2:10][CH2:11][C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:23]1[CH2:29][CH2:28][CH2:27][C@H:24]1[CH2:25][OH:26].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:22])[CH2:10][CH2:11][C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([N:23]1[CH2:29][CH2:28][CH2:27][C@H:24]1[CH2:25][OH:26])=[O:18])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 640091L-ProlinolHCID 70041574HCID 70041574, compound

Product 1

HCID 70041852HCID 70041852, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(benzyloxysuccinyl)-L-proline (152.5 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 over a period of 40 minutes under water-cooling. The mixture is stirred for a further three hours at room temperature. 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), and the organic layer is dried over anhydrous magnesium sulfate and filtered. The filtrate is concentrated to dryness under reduced pressure and the residue is purified by column chromatography on silica gel (chloroform:methanol) to give N-(benzyloxysuccinyl)-L-prolyl-prolinol (90 g, 46.4%).

Workup

  1. temperatureover a period of 40 minutes under water-cooling
  2. customThe reaction liquid
  3. washis washed successively with water (1 l)
  4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate (1 l), 1N hydrochloric acid (1 l) and water (1 l), and the organic layer is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated to dryness under reduced pressure
  7. customthe residue is purified by column chromatography on silica gel (chloroform:methanol)

Sources & evidence

ORD record
ord-fb74cb2289e64f719b963964765fc388
Source dataset
uspto-grants-1992_10
Patent number
US05158970

Reaction notes

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