Lithium Hydroxide → HCID 22874287, compound

HRID 1377186Notes

Reaction equation

HRID 1377186 reaction equation
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH3:31])[CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-:32].[Li+]>C(COC)OC.O.C(OCC)(=O)C.C1COCC1>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@@H:17]([OH:32])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31])[C:20]([OH:21])=[O:22])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 70149726HCID 70149726, compound

Product 1

HCID 22874287HCID 22874287, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 474 mg of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(2-methoxyphenyl)methyl]dihydrofuran-2-(3H)-one in 18 ml of dimethoxyethane and 9.07 ml of water is treated dropwise, at RT, with 4.45 ml of a 1M lithium hydroxide solution. After that, the reaction mixture is stirred at RT for 3 h and diluted with ethyl acetate and THF, and the whole is washed in a separating funnel until neutral with a mixture consisting of 54.78 ml of sat. ammonium chloride solution and 4.58 ml of 10% citric acid solution, followed by saline and water. The title compound, which is subjected to further processing without any further purification, is obtained after drying over sodium sulfate and removing the solvent. TLC Rf (hexane/ethyl acetate 2.5:1)=0.15.

Workup

  1. washthe whole is washed in a separating funnel until neutral with a mixture
  2. customThe title compound, which is subjected to further processing without any further purification
  3. customis obtained
  4. dry with materialafter drying over sodium sulfate
  5. customremoving the solvent

Sources & evidence

ORD record
ord-2d8d157c57984499b4229614680fb141
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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