Sodium Hydroxide → (S)-5-[Bis[2-(Boc-amino)ethyl]amino]-2-(Boc-amino)-5-oxopentanoic Acid

HRID 1425907Notes

Reaction equation

HRID 1425907 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:12]([CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]([O:19]C)=[O:18])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:12](=[O:13])[CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:17]([OH:19])=[O:18])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59366631Methyl N2-(tert-butoxycarbonyl)-N5,N5-bis(2-((tert-butoxycarbonyl)amino)ethyl)-L-glutaminate

Product 1

HCID 59366705(S)-5-[Bis[2-(Boc-amino)ethyl]amino]-2-(Boc-amino)-5-oxopentanoic AcidYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of the ester (XV) (290 mg, 0.51 mmol) in MeOH (10 mL) was added 4 M NaOH dropwise until pH=13. The mixture was stirred overnight at room temperature before evaporating the MeOH under reduced pressure. The residue was mixed with water and washed with ether. After acidifying to pH˜3 with 2 M HCl, the product was extracted with DCM, dried over MgSO4 and concentrated under vacuum to give (S)-5-(bis(2-(tert-butoxycarbonylamino)ethyl)amino)-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid (XVI) (250 mg, 0.45 mmol, 88% yield). ESIMS found for C24H44N4O9 m/z 533 (M+H).

Workup

  1. custombefore evaporating the MeOH under reduced pressure
  2. additionThe residue was mixed with water
  3. washwashed with ether
  4. extractionthe product was extracted with DCM
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3b0e5cdb6c8a4f31b52bb11876dca766
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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