Lithium Hydroxide → (S)-4-((S)-3-Carboxy-2-hydroxy-propyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

HRID 2095497Notes

Reaction equation

HRID 2095497 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]([OH:24])[CH2:19][C:20]([O:22]C)=[O:21])[C:13](=[O:25])[C@@H:12]1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]([OH:24])[CH2:19][C:20]([OH:22])=[O:21])[C:13](=[O:25])[C@@H:12]1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 67074026(S)-4-((S)-2-Hydroxy-3-methoxycarbonyl-propyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 67074047(S)-4-((S)-3-Carboxy-2-hydroxy-propyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl esterYield 81%

Procedure

In analogy to the procedure described in Example 23B, (S)-4-((S)-2-hydroxy-3-methoxycarbonyl-propyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester and 1 M aq. lithium hydroxide solution gave after extraction with EtOAc and precipitation (dichloromethane/n-pentane) the titled compound in 81% yield as light yellow waxy solid. MS: 351.15 (MH+).

Workup

  1. customgave
  2. extractionafter extraction
  3. customwith EtOAc and precipitation (dichloromethane/n-pentane) the titled compound in 81% yield as light yellow waxy solid

Sources & evidence

ORD record
ord-ae12123cbb854d96a8a5c02f7238977b
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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