Lithium Hydroxide → HCID 66871907, compound

HRID 1620380Notes

Reaction equation

HRID 1620380 reaction equation
[OH-].[Li+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][CH2:21][C@H:22]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:23]([O:25]C)=[O:24])(=[O:19])=[O:18])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1.O>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][CH2:21][C@H:22]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:23]([OH:25])=[O:24])(=[O:19])=[O:18])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67494711HCID 67494711, compound

Product 1

HCID 66871907HCID 66871907, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.6 ml (1.6 mmol) of an aqueous solution of lithium hydroxide having a concentration of 1N are added to a solution of 450 mg (1.1 mmol) of methyl(S)-3-(4-benzyloxybenzenesulfonylamino)-2-piperidin-1-ylpropanoate in 15 ml of tetrahydrofuran and 0.5 ml of water. After stirring at ambient temperature for 18 h, the tetrahydrofuran is evaporated off under vacuum and then 1.8 ml of an aqueous solution of acetic acid having a concentration of 1N and 15 ml of water are added. The product precipitates and is filtered off. 420 mg (98%) of (S)-3-(4-benzyloxybenzenesulfonylamino)-2-piperidin-1-ylpropanoic acid are obtained in the form of a white solid.

Workup

  1. customthe tetrahydrofuran is evaporated off under vacuum
  2. addition1.8 ml of an aqueous solution of acetic acid having a concentration of 1N and 15 ml of water are added
  3. customThe product precipitates
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-766f765190084c8a8d022f5b4d0d64ac
Source dataset
uspto-grants-2014_07
Patent number
US08772478B2

Reaction notes

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