Acetic Acid → HCID 23510743, compound

HRID 1883301Notes

Reaction equation

HRID 1883301 reaction equation
C([NH:11][CH2:12][CH:13]([N:15]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])C)(OCC1C=CC=CC=1)=O.[C:32]([OH:35])(=[O:34])[CH3:33]>C(O)C.[Ni]>[C:17]([OH:19])(=[O:18])[CH3:16].[C:32]([OH:35])(=[O:34])[CH3:33].[C:28]([O:27][C:25]([CH2:24][N:15]([CH2:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][CH:12]([NH2:11])[CH3:32])=[O:26])([CH3:29])([CH3:30])[CH3:31]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 23510759HCID 23510759, compound

Product 1

HCID 23510743HCID 23510743, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of N-carbobenzyloxy-N′,N′-bis-(t-butoxycarbonylmethyl)-propylenediamine 35 (5.3017 g, 12.144 mmol) in ethanol (75 mL) was filtered through a bed of Raney nickel into a solution of acetic acid (2.1 mL, 3 equiv) in ethanol (75 mL). The filtrate was degassed with nitrogen and treated with 10% palladized charcoal (0.4 g). The mixture was hydrogenated at 50 psi on a Parr apparatus for 16 h and then the catalyst was filtered off on a bed of celite. The filtrate was concentrated in vacuo and the residue flushed with chloroform (150 mL). The crude product was carried on without further purification.

Workup

  1. customThe filtrate was degassed with nitrogen
  2. additiontreated with 10% palladized charcoal (0.4 g)
  3. filtrationthe catalyst was filtered off on a bed of celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue flushed with chloroform (150 mL)
  6. customThe crude product was carried on without further purification

Sources & evidence

ORD record
ord-2d111374f73b4e098e8cd2b0f794590a
Source dataset
uspto-grants-2004_07
Patent number
US06759509B1

Reaction notes

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