Lithium Hydroxide → HCID 86647502, compound

HRID 389184Notes

Reaction equation

HRID 389184 reaction equation
[Li+].[OH-].[CH3:3][C:4]([CH3:27])([CH2:24][CH:25]=[CH2:26])[CH2:5][N:6]([CH3:23])[C:7]([NH:9][C@@H:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[C:11]([O:13]CC)=[O:12])=[O:8]>CO.O.C1COCC1>[CH3:3][C:4]([CH3:27])([CH2:24][CH:25]=[CH2:26])[CH2:5][N:6]([CH3:23])[C:7]([NH:9][C@@H:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[C:11]([OH:13])=[O:12])=[O:8]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 59571145HCID 59571145, compound

Product 1

HCID 86647502HCID 86647502, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (66 mmol) was added to a solution of ethyl (2S)-2-({[(2,2-dimethylpent-4-en-1-yl)(methyl)amino]carbonyl}amino)non-8-enoate (2.35 g, 6.67 mmol) in MeOH (20 mL), water (10 mL) and THF (30 mL). The reaction mixture was stirred for 3 hours at RT and then concentrated. A solution 5% potassium bisulfate was added, and the mixture was extracted with EtOAc (3×). The combined organic were washed with brine, dried over MgSO4, filtered and concentrated to give the title compound. LRMS (M+H)+=325.3.

Workup

  1. concentrationconcentrated
  2. additionA solution 5% potassium bisulfate was added
  3. extractionthe mixture was extracted with EtOAc (3×)
  4. washThe combined organic were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bcd625b49b9540f68888502164062ae0
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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