Water → HCID 10507094, compound

HRID 1871666Notes

Reaction equation

HRID 1871666 reaction equation
[NH:1]([C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[C@H:2]([C:6]([NH:8][C@H:9]([C:13]([N:15]([CH3:31])[C@H:16]([C:20]([N:22]1[CH2:30][CH2:29][CH2:28][C@H:23]1[C:24]([O:26]C)=[O:25])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[Li+].[OH-].O>CO>[NH:1]([C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[C@H:2]([C:6]([NH:8][C@H:9]([C:13]([N:15]([CH3:31])[C@H:16]([C:20]([N:22]1[CH2:30][CH2:29][CH2:28][C@H:23]1[C:24]([OH:26])=[O:25])=[O:21])[CH:17]([CH3:19])[CH3:18])=[O:14])[CH:10]([CH3:11])[CH3:12])=[O:7])[CH:3]([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 15291044HCID 15291044, compound

Product 1

HCID 10507094HCID 10507094, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

31.96 g (57 mmol) Z-Val-Val-MeVal-Pro-OMe were dissolved in 250 ml methanol. 102.6 ml of a 1 N LiOH solution was added and the mixture stirred overnight at room temperature. After addition of 500 ml water, the aqueous phase was washed three times with ethyl acetate, adjusted to pH 2 at 0° C. and extracted three times with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and evaporated to dryness yielding 30.62 g of the desired product as a white solid.

Workup

  1. washthe aqueous phase was washed three times with ethyl acetate
  2. customadjusted to pH 2 at 0° C.
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-349ad30411004813ab6a72f59691fce3
Source dataset
uspto-grants-2000_08
Patent number
US06103698

Reaction notes

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