Water → HCID 7019898, compound

HRID 2399239Notes

Reaction equation

HRID 2399239 reaction equation
[NH:1]1[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].C(N(CC)CC)C.O.[CH3:28][C:29]([O:32][C:33](ON=C(C1C=CC=CC=1)C#N)=[O:34])([CH3:31])[CH3:30]>CC(C)=O>[N:1]1([C:33]([O:32][C:29]([CH3:31])([CH3:30])[CH3:28])=[O:34])[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 635194613589-02-1

Product 1

HCID 7019898HCID 7019898, compoundYield 144.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of L-Pro-L-Phe (1.0 g, 3.8 mmol) and triethylamine (0,794 ml, 5.7 mmol) in 1:1 water:acetone (38 ml) was added Boc-ON (1.13 g, 4.6 mmol), and the reaction mixture stirred at room temperature for 9 hours. Acetone was removed by evaporation under reduced pressure and the resulting aqueous solution diluted with a solution of saturated sodium bicarbonate and then washed with ether. The remaining aqueous phase was acidified to pH 2.0 and extensively extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated to yield 1.99 g of N-Boc-L-Pro-L-Phe as a white glassy solid.

Workup

  1. customAcetone was removed by evaporation under reduced pressure
  2. additionthe resulting aqueous solution diluted with a solution of saturated sodium bicarbonate
  3. washwashed with ether
  4. extractionextensively extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f7d86fc86cc451694bc03833cc93d39
Source dataset
uspto-grants-1995_09
Patent number
US05447915

Reaction notes

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