Sodium Hydroxide → HCID 178520544, compound

HRID 2210475Notes

Reaction equation

HRID 2210475 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:30])[CH2:7][CH:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:9]([NH:11][C@@H:12]([C:19]([O:21]C)=[O:20])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=[O:10].[OH-].[Na+]>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:30])[CH2:7][CH:8]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:9]([NH:11][C@@H:12]([C:19]([OH:21])=[O:20])[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501403HCID 178501403, compound

Product 1

HCID 178520544HCID 178520544, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0,581 g of methyl (R)-N-[4-(2-furanyl)-1,4-dioxo-2-(phenylmethyl)butyl]-L-histidinate, 1.8 ml of methanol and 1.8 ml of 1N sodium hydroxide is stirred at room temperature for 2 hours. The solvent is removed, water added and the pH adjusted to pH 4 to pH 5. The mixture is extracted with dichloromethane (5×10 ml), the extract dried (Na2SO4) and the solvent removed to give 0.26 g of product as a white foam. The aqueous layer is extracted again with ethyl acetate (3×10 ml) and with chloroform containing 1% CH3OH. The ethyl acetate and chloroform extracts are combined, dried (Na2SO4) and the solvent removed to give 0.21 g of product as a white foams [α]D26 +25°±1 (c, 0.92, CH30H).

Workup

  1. customThe solvent is removed
  2. additionwater added
  3. extractionThe mixture is extracted with dichloromethane (5×10 ml)
  4. dry with materialthe extract dried (Na2SO4)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-c281eae30c2e46098deb1d31b09c428a
Source dataset
uspto-grants-1995_10
Patent number
US05459131

Reaction notes

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