Lithium hydroxide, monohydrate → HCID 69820413, compound

HRID 1840517Notes

Reaction equation

HRID 1840517 reaction equation
[CH3:1][C:2]([CH3:32])([O:4][C:5]([NH:7][C@@H:8]([CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:18][CH2:17]1)[C:9]([O:11]C)=[O:10])=[O:6])[CH3:3].O.[OH-].[Li+]>CO.O>[CH3:3][C:2]([CH3:32])([O:4][C:5]([NH:7][C@@H:8]([CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23])[CH2:18][CH2:17]1)[C:9]([OH:11])=[O:10])=[O:6])[CH3:1]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86590129HCID 86590129, compound

Product 1

HCID 69820413HCID 69820413, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3.55 g (8.0 mmol) of methyl (S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-1-[(phenylmethoxy)carbonyl]piperidine-4-pentanoate and 0.40 g (9.6 mmol) of lithium hydroxide monohydrate in 15 ml of methanol and 5 ml of water is stirred for 18 h at room temperature. The methanol is evaporated off under reduced pressure and the mixture is then cooled to 0° C. and acidified to pH 2 with aqueous 1N hydrochloric acid solution, and then extracted twice with 150 ml of ethyl acetate. The resulting extract is washed with 100 ml of saturated sodium chloride solution and then dried over sodium sulphate and filtered, and the residue obtained is concentrated. 3 g of (S)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-1-[(phenylmethoxy)carbonyl]piperidine-4-pentanoic acid are obtained in the form of a white powder, which is used without further purification in the following step.

Workup

  1. customThe methanol is evaporated off under reduced pressure
  2. temperaturethe mixture is then cooled to 0° C.
  3. extractionextracted twice with 150 ml of ethyl acetate
  4. extractionThe resulting extract
  5. washis washed with 100 ml of saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customthe residue obtained
  9. concentrationis concentrated

Sources & evidence

ORD record
ord-dbca07a9155d4958b4b8a4ace961e862
Source dataset
uspto-grants-2004_01
Patent number
US06680329B2

Reaction notes

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