Triethylamine → HCID 54559759, compound

HRID 487427Notes

Reaction equation

HRID 487427 reaction equation
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(Cl)(Cl)=[NH2+].[Cl-].[C:24]([O:28][C:29](=[O:46])[CH2:30][N:31]1[CH2:36][CH2:35][NH:34][C@@H:33]([CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:32]1=[O:45])([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[C:24]([O:28][C:29](=[O:46])[CH2:30][N:31]1[CH2:36][CH2:35][N:34]([C:13](=[O:15])[C@@H:12]2[CH2:16][CH2:17][CH2:18][N:11]2[C:1]([O:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])[CH:33]([CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:32]1=[O:45])([CH3:25])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 10568286HCID 10568286, compoundHCID 21460054HCID 21460054, compound

Product 1

HCID 54559759HCID 54559759, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

In 20 ml of dimethylformamide was dissolved 1.25 g of carbobenzyloxy-L-proline. The solution was cooled to -10° C., then there was added 810 mg of phosgene iminium chloride, and the mixture was stirred for 2 hours. To the mixture were added dropwise 5 ml of dimethylformamide containing 1.8 g of (S)-2-oxopiperazine-1,3-diacetic acid di-t-butyl ester synthesized in Working Example 3, then 2 ml of triethylamine. The mixture was stirred for one hour. The reaction mixture was diluted with ethyl acetate and was poured into ice-water. The organic layer was washed with a 5% potassium hydrogensulfate and a saturated aqueous solution of sodium hydrogenphosphate. The extract solution was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to give a crude product. The crude product was purified by s silica gel chromatography (ethyl acetate) to afford 1.0 g of the title compound as amorphous powder.

Workup

  1. customsynthesized in Working Example 3
  2. stirringThe mixture was stirred for one hour
  3. washThe organic layer was washed with a 5% potassium hydrogensulfate
  4. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  5. concentrationwas concentrated under reduced pressure
  6. customto give a crude product
  7. customThe crude product was purified by s silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b1912f255e4249fba94b5b7933830bf5
Source dataset
uspto-grants-1994_03
Patent number
US05294713

Reaction notes

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