Ammonium formate → HCID 21043752, compound

HRID 628689Notes

Reaction equation

HRID 628689 reaction equation
C(OC([C@H:8]([C:17]([NH:19][C@H:20]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[CH3:21])=[O:18])[CH2:9][CH2:10][CH2:11][N:12](N)C(=O)[O-])=O)(C)(C)C.[CH:32]([O-:34])=[O:33].[NH4+:35]>C(O)C.[Pd]>[NH2:12][CH2:11][CH2:10][CH2:9][C@H:8]([NH:35][C:32](=[O:34])[O:33][C:22]([CH3:31])([CH3:23])[CH3:20])[C:17]([NH:19][C@H:20]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[CH3:21])=[O:18]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 131735355HCID 131735355, compound

Product 1

HCID 21043752HCID 21043752, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A solution of (S)-4-(tert-butoxycarbonyl)-amino-5-((S)-1-(naphthalen-1-yl)ethylamino)-5-oxopentylcarbamate, 23, (28.0 g, 54.0 mmol) in ethanol (600 mL) was added ammonium formate (10.2 g, 160.0 mmol) and palladium (10 wt % on carbon, 1.0 g). The reaction mixture was warmed to 55° C. and stirred for 18 h at 55° C. The mixture was filtered through Celite and washed with ethanol. The resulting filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate and the organic phase was washed with aqueous saturated NaCl solution. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The crude residue was used without further purification: 1H NMR (d6-DMSO) δ 8.55 (d, J=7.6 Hz, 1H), 8.04 (d, J=8.4 Hz, 1H), 7.89 (d, J=8.0 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.53-7.42 (m, 4H), 6.81 (d, J=8.0 Hz, 1H), 5.65-5.62 (m, 1H), 3.96-3.89 (m, 1H), 2.60-2.53 (m, 2H), 1.46-1.40 (m, 7H), 1.33 (s, 9H); ESI+ MS: m/z (rel intensity) 386.2 (100, [M+H]+).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with ethanol
  3. concentrationThe resulting filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic phase was washed with aqueous saturated NaCl solution
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was used without further purification

Sources & evidence

ORD record
ord-ee4af1afb05d4a55bf9a1e14ee8e659d
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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