HCID 89524899, compound → HCID 89524967, compound

HRID 706348Notes

Reaction equation

HRID 706348 reaction equation
I[C:2]1[O:3][CH:4]=[C:5]([C:7]2[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=2[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[N:6]=1>CCO.[Pd]>[O:3]1[CH:4]=[C:5]([C:7]2[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=2[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[N:6]=[CH:2]1

Participants

4

Reactant 1

HCID 89524899HCID 89524899, compound

Product 1

HCID 89524967HCID 89524967, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogenolysis of the tert-butyl 2-(2-iodooxazol-4-yl)benzylcarbamate was performed using H-Cube, 10% Pd/C, full H2 Mode, at 25° in EtOH. Following completion the reaction was concentrated and the residue was purified via Biotage (0% to 10% gradient; EtOAc:Hex; 50 g-HP-silica gel column). Obtained 200 mg of tert-butyl 2-(oxazol-4-yl)benzylcarbamate. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47 (s, 9H) 4.39 (s, 2H) 7.36 (ddd, J=7.26, 5.37, 1.77 Hz, 2H) 7.48-7.65 (m, 2H) 7.89 (d, J=1.01 Hz, 1H) 8.00 (s, 1H); MS[MH]+=275.2

Workup

  1. customat 25°
  2. concentrationwas concentrated
  3. customthe residue was purified via Biotage (0% to 10% gradient; EtOAc:Hex; 50 g-HP-silica gel column)

Sources & evidence

ORD record
ord-69b44956812d4f778955e8333f68479d
Source dataset
uspto-grants-2015_11
Patent number
US09174984B2

Reaction notes

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