Lithium Hydroxide → HCID 22876405, compound

HRID 2394125Notes

Reaction equation

HRID 2394125 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][C:27]3[O:30][CH2:31][O:32][C:26]=3[CH:25]=2)[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.[OH-:33].[Li+].C[O:36]CCOC>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:21])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1)[C:20]([OH:22])=[O:36])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:33]

Participants

7

Reactant 3

HCID 3939Lithium HydroxideHCID 80711,2-DimethoxyethaneHCID 70149639HCID 70149639, compound

Product 1

HCID 22876405HCID 22876405, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 278 mg of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(3,4-methylenedioxyphenyl)methyl]dihydrofuran-2-(3H)-one in 10.25 ml of ethylene glycol dimethyl ether and 5.15 ml of water is treated dropwise, at RT, with 2,53 ml of a 1M lithium hydroxide solution. After that, the reaction mixture is stirred at RT for 3 h, diluted with ethyl acetate and THF, and washed in a separating funnel until neutral with a mixture consisting of 31 ml of sat. ammonium chloride solution and 2.6 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. FAB-MS (M+H)+ =458.

Workup

  1. washwashed 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-c035ee1b931a40d9a499c6bcd6ac1cbd
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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