Trifluoroacetic acid → HCID 67875849, compound

HRID 483860Notes

Reaction equation

HRID 483860 reaction equation
[CH2:1]([O:8][C:9](=[O:37])[C@H:10]([CH3:36])[NH:11][C:12](=[O:35])[C@H:13]([CH:23]([C:28](=[O:34])[C@H:29]([CH:31]([CH3:33])[CH3:32])[NH2:30])[C:24]([F:27])([CH3:26])[CH3:25])[N:14](C(OC(C)(C)C)=O)[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:37])[C@H:10]([CH3:36])[NH:11][C:12](=[O:35])[C@H:13]([CH:23]([C:28](=[O:34])[C@H:29]([CH:31]([CH3:33])[CH3:32])[NH2:30])[C:24]([F:27])([CH3:25])[CH3:26])[NH:14][CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 131718026HCID 131718026, compound

Product 1

HCID 67875849HCID 67875849, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.75 g (0.0033 mole) of Boc-4-fluoro-3(R,S)-L-Valyl-N-Methyl-L-Leucyl-L-Alanine benzyl ester in 17 ml of dry methylene chloride was stirred and cooled at -10° C. as 17 ml of trifluoroacetic acid, which was previously cooled at the same temperature, was added. The reaction was stirred and kept at -5° C. for 16 hours, then poured carefully with stirring into a mixture of 21 g of sodium bicarbonate, ice, and 100 ml of methylene chloride. After 5 minutes the organic layer was separated and washed with 3×30 ml of saturated sodium bicarbonate solution. The methylene chloride layer was dried over magnesium sulfate, and evaporated in vacuo to give 1.38 g of a stiff oil as the product. The yield was 99% of theory and the FAB m.s. showed a molecular ion peak at 424.

Workup

  1. temperaturewas previously cooled at the same temperature
  2. additionwas added
  3. additionpoured carefully
  4. customAfter 5 minutes the organic layer was separated
  5. washwashed with 3×30 ml of saturated sodium bicarbonate solution
  6. dry with materialThe methylene chloride layer was dried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6e65c7ce46184235b64283ef28154993
Source dataset
uspto-grants-1993_07
Patent number
US05227467

Reaction notes

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