Trifluoroacetic acid → N-Methyl-L-Leucyl-L-Valyl-N-Methyl-L-Alanyl-L-Alanine Benzyl Ester

HRID 2072759Notes

Reaction equation

HRID 2072759 reaction equation
[CH2:1]([O:8][C:9](=[O:42])[C@H:10]([CH3:41])[NH:11][C:12](=[O:40])[C@H:13]([CH3:39])[N:14]([C:16](=[O:38])[C@H:17]([CH:35]([CH3:37])[CH3:36])[NH:18][C:19](=[O:34])[C@H:20]([CH2:30][CH:31]([CH3:33])[CH3:32])[N:21](C(OC(C)(C)C)=O)[CH3:22])[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+]>ClCCl>[CH2:1]([O:8][C:9](=[O:42])[C@H:10]([CH3:41])[NH:11][C:12](=[O:40])[C@H:13]([CH3:39])[N:14]([C:16](=[O:38])[C@H:17]([CH:35]([CH3:36])[CH3:37])[NH:18][C:19](=[O:34])[C@H:20]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:21][CH3:22])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 14673110Boc-N-Methyl-L-Leucyl-L-Valyl-N-Methyl-L-Alanyl-L-Alanine Benzyl Ester

Product 1

HCID 14673112N-Methyl-L-Leucyl-L-Valyl-N-Methyl-L-Alanyl-L-Alanine Benzyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of 15.7 g (0.0266 mole) of Boc-N-methyl-L-leucyl-L-valyl-N-methyl-L-alanyl-L-alanine benzyl ester in 125 ml of dry dichloromethane was stirred and cooled to -10° C. while 70 ml trifluoroacetic acid, previously cooled at -15° C., was added. After 2 hours, the reaction was carefully added with good stirring to a mixture of 105 g of sodium bicarbonate, ice, and 200 ml of dichloromethane. The organic layer was separated and the aqueous layer was extracted with another 50 ml of dichloromethane. The combined organic layers were washed with 3×80 ml of saturated sodium bicarbonate solution, dried over magnesium fulfate, and evaporated leaving 11.85 g (91% of theory) of product. The FAB m.s. showed a molecular ion peak at 491.

Workup

  1. additionwas added
  2. additionthe reaction was carefully added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with another 50 ml of dichloromethane
  5. washThe combined organic layers were washed with 3×80 ml of saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium fulfate
  7. customevaporated
  8. customleaving 11.85 g (91% of theory) of product

Sources & evidence

ORD record
ord-d2756f6f1d614957804b5ed4c06a9769
Source dataset
uspto-grants-1990_04
Patent number
US04914188

Reaction notes

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