Sodium Hydroxide → HCID 131720454, compound

HRID 861316Notes

Reaction equation

HRID 861316 reaction equation
[NH:1]([C:30]([CH3:32])=[O:31])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:26]([O:28]C)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[OH-].[Na+]>CO>[NH:1]([C:30]([CH3:32])=[O:31])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:26]([OH:28])=[O:27])[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:16])[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131720455HCID 131720455, compound

Product 1

HCID 131720454HCID 131720454, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Conversion to the Free Acid. Ac-Leu-Leu-Phe-OMe was dissolved in 150 mL of methanol and 26 mL of 1N sodium hydroxide was added and the rection was stirred 4 hours at which time the methanol was removed under reduced pressure and an additional 7 mL of sodium hydroxide was added. This water fraction was then washed with ethyl acetate (10 mL) and neutralized by the addition of 1N HCL. The resulting mixture was extracted with ethyl acetate 2×100 mL and the extract washed with 1N HCL, brine and dried over MgSO4, filtered and the solvents were removed under reduced pressure to give 7.56 g (94%) of Ac-Leu-Leu-Phe-OH as a white solid. The NMR (100 MHz, CDCl3) of the product acid bears striking resemblance to that of the precursor ester except for the loss of a signal at δ 3.6 and the appearance of a broad singlet at 10.1 (1H).

Workup

  1. customwas removed under reduced pressure
  2. additionan additional 7 mL of sodium hydroxide was added
  3. washThis water fraction was then washed with ethyl acetate (10 mL)
  4. additionneutralized by the addition of 1N HCL
  5. extractionThe resulting mixture was extracted with ethyl acetate 2×100 mL
  6. washthe extract washed with 1N HCL, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-a5e64337ab15496bba7b12ee6d4e7a99
Source dataset
uspto-grants-1998_02
Patent number
US05714484

Reaction notes

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