Ammonium formate → HCID 90388842, compound

HRID 64507Notes

Reaction equation

HRID 64507 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][C@H:34]([NH:42][C:43](=[O:62])[NH:44][C@@H:45]([CH2:53][CH2:54][C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:28])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:38]([O:37][C:35](=[O:36])[C@@H:34]([NH:42][C:43](=[O:62])[NH:44][C@@H:45]([CH2:53][CH2:54][C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[C:46]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:47])[CH2:33][CH2:32][CH2:31][CH2:30][NH:29][C:27](=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)([CH3:39])([CH3:40])[CH3:41]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 90388748HCID 90388748, compound

Product 1

HCID 90388842HCID 90388842, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)-di-tert-butyl 2-(3-((S)-6-(11-(4-((benzyloxy)carbonyl)piperazin-1-yl)undecanamido)-1-(tert-butoxy)-1-oxohexan-2-yl)ureido)pentanedioate (1.50 g, 1.72 mmol) and ammonium formate (1.0 g) in ethanol (60 mL) was added palladium on carbon (300 mg). The reaction mixture was stirred at room temperature for overnight and filtered through a pad of celite followed by washing of the celite pad using ethyl acetate (EtOAc). The solvent was removed under reduced pressure and the residue dissolved in dichloromethane (DCM). The DCM solution was washed using saturated sodium bicarbonate and then partitioned to separate the organic layer from the aqueous layer. Concentration of the organic layer under reduced pressure afforded the titled product as a yellowish solid (1.2345 g, 97% yield). MS (ESI), 740.4 (M+H)+.

Workup

  1. filtrationfiltered through a pad of celite
  2. washby washing of the celite pad
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in dichloromethane (DCM)
  5. washThe DCM solution was washed
  6. custompartitioned
  7. customto separate the organic layer from the aqueous layer

Sources & evidence

ORD record
ord-eacbcaac9ca04da982b46436d2a5d9da
Source dataset
uspto-grants-2016_09
Patent number
US09447121B2

Reaction notes

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