Lithium hydroxide, monohydrate → HCID 58232143, compound

HRID 2095588Notes

Reaction equation

HRID 2095588 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:10][N:9]([C:11](=[O:21])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH:8]([CH3:22])[C:7](=[O:23])[N:6]1[CH2:24][CH2:25][CH2:26][C:27]([N:29]1[CH2:36][CH2:35][C:32]2([CH2:34][CH2:33]2)[C@H:31]([OH:37])[CH2:30]1)=[O:28])=[O:4].O.[OH-].[Li+]>CO>[Cl:20][C:15]1[CH:14]=[C:13]([NH:12][C:11]([N:9]2[C@@H:8]([CH3:22])[C:7](=[O:23])[N:6]([CH2:24][CH2:25][CH2:26][C:27]([N:29]3[CH2:36][CH2:35][C:32]4([CH2:33][CH2:34]4)[C@H:31]([OH:37])[CH2:30]3)=[O:28])[CH:5]([C:3]([OH:4])=[O:2])[CH2:10]2)=[O:21])[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67074551HCID 67074551, compound

Product 1

HCID 58232143HCID 58232143, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.15 g (0.26 mmol) of (S)-4-(3,4-dichloro-phenylcarbamoyl)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-5-methyl-6-oxo-piperazine-2-carboxylic acid methyl ester in 2 ml of MeOH was added 0.01 g (0.26 mmol) of lithium hydroxide monohydrate. The reaction was stirred for 16 h after which time Amberlite IR120 resin was added until the pH was 5 and the reaction filtered and concentrated to afford the titled compound in 73% yield, a 6:4 mixture of diasteriomers as a colorless gum. MS: 541.3 (MH+, 2Cl).

Workup

  1. additionwas added until the pH was 5
  2. filtrationthe reaction filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d207bb7f90e6497f937b894826d74f7b
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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